Photochromic articles that activate behind ultraviolet radiation blocking transparencies and methods for preparation

ABSTRACT

Described are photochromic articles that include a substrate and a photochromic amount of at least one organic photochromic material (b) represented by graphic formula XIII adapted to change from an unactivated state to an activated state by exposure to radiation substantially in a wavelength range from 380 to 410 nanometers (nm) when measured over a wavelength range of from 380 to 700 nm. The photochromic articles demonstrate a photochromic response when activated behind an ultraviolet blocking transparency such as an automotive windshield. For example, the photochromic articles retain at least 12 percent of the activation measured as change in optical density or delta OD under outdoor simulating conditions in the Outdoor Test when tested under conditions simulating an eyeglass wearer behind an automotive windshield in the Behind the Windshield Test. Methods for producing the aforedescribed photochromic articles are also described.

BACKGROUND OF THE INVENTION

The present invention relates to novel photochromic articles thatactivate or become darker behind an ultraviolet radiation blockingtransparency, e.g., an automotive windshield. More particularly, thisinvention relates to photochromic articles that demonstrate activatedcoloration or darkness when tested under conditions simulating aneyeglass wearer behind an automotive windshield and at least 70 percenttransmittance in the unactivated state.

Photochromism is a phenomenon involving a light induced reversiblechange in color. An article containing such a material that becomescolored upon exposure to light radiation containing ultraviolet rayswill revert to the original color when the influence of the ultravioletradiation is discontinued. Sources of light radiation that containultraviolet rays include, for example, sunlight and the light of amercury lamp. Discontinuation of the ultraviolet radiation can beachieved for example by storing the photochromic material or article inthe dark or by removing the source of ultraviolet radiation, e.g., bymeans of filtering.

Typical photochromic articles do not activate or demonstrate negligibleactivation behind automotive windshields due to the limited ultravioletradiation available for activation. A photochromic article that has beendisclosed to function behind such ultraviolet radiation blockingtransparencies includes photochromic compounds that activate by means oflight in the visible spectrum. Such an article requires the presence ofultraviolet light absorbers to prevent the article from becoming toodark when not behind the windshield. The unactivated state of such anarticle is colored resulting in a percent transmission less than 70percent.

The present invention provides a photochromic article that activatesbehind ultraviolet radiation blocking transparencies and a method forpreparing such articles using photochromic materials that have beenadapted to change from an unactivated form to an activated form byexposure to activating radiation substantially in the range of from 380to 410 nanometers (nm), when such activating radiation is measured overa range from 380 to 700 nm.

BRIEF DESCRIPTION OF THE FIGURE

FIG. 1 shows the spectrum of the light passing through the automotivewindshield simulating system used in the Behind the Windshield Testdescribed herein in Example 13.

DETAILED DESCRIPTION OF THE INVENTION

It is noted that, as used in this specification and the appended claims,the singular forms “a,” “an,” and “the” include plural referents unlessexpressly and unequivocally limited to one referent.

For the purposes of this specification, unless otherwise indicated, allnumbers expressing quantities of ingredients, reaction conditions, andother parameters used in the specification and claims are to beunderstood as being modified in all instances by the term “about”.Accordingly, unless indicated to the contrary, the numerical parametersset forth in the following specification and attached claims areapproximations that may vary depending upon the desired propertiessought to be obtained by the present invention. At the very least, andnot as an attempt to limit the application of the doctrine ofequivalents to the scope of the claims, each numerical parameter shouldat least be construed in light of the number of reported significantdigits and by applying ordinary rounding techniques.

Notwithstanding that the numerical ranges and parameters setting forththe broad scope of the invention are approximations, the numericalvalues set forth in the specific examples are reported as precisely aspossible. Any numerical value, however, inherently contain certainerrors necessarily resulting from the standard deviation found in theirrespective testing measurements.

The phrase “an at least partial coating” means an amount of coatingcovering from a portion to the complete surface of the substrate. Thephrase “an at least partially cured coating” refers to a coating inwhich the curable or cross-linkable components are from at leastpartially cured up to fully cured, crosslinked and/or reacted. Inalternate non-limiting embodiments of the present invention, the degreeof reacted components can vary widely, e.g., from 5% to 100% of all thepossible curable, crosslinkable and/or reactable components.

The phrase “an at least partially abrasion resistant coating or film”refers to a coating or film that demonstrates a resistance to abrasionthat is greater than the standard reference material, typically aplastic made of CR-39® monomer available from PPG Industries, Inc, astested in a method comparable to ASTM F-735 Standard Test Method forAbrasion Resistance of Transparent Plastics and Coatings Using theOscillating Sand Method. The phrase “an at least partiallyantireflective coating” is a coating that at least partially improvesthe antireflective nature of the surface to which it is applied byincreasing the percent transmittance as compared to an uncoated surface.The improvement in percent transmittance can range from 1 to 9 percentabove the uncoated surface. Put another way, the percent transmittanceof the coated surface can range from a percentage greater than theuncoated surface up to 99.9.

In one non-limiting embodiment, the use of at least one photochromicmaterial adapted to change from an unactivated form to an activated formby exposure to activating radiation substantially in the wavelengthrange of from 380 to 410 nm in a photochromic article tested in theBehind the Windshield Test adapts the photochromic article to retain atleast 12 percent of the coloration, measured as delta OD or ΔOD, thatwould have occurred if the adapted photochromic article was activatedunder conditions simulating outdoor exposure as described in the OutdoorTest in Example 13 herein.

In another non-limiting embodiment, the adapted photochromic articleretains at least 20 percent of the coloration. In a further non-limitingembodiment, the adapted photochromic article retains at least 25 percentof the coloration exhibited in the Outdoor Test when tested in theBehind the Windshield Test. The coloration or percent ΔOD retained bythe adapted photochromic article of the present invention can rangebetween any combination of these values, inclusive of the recited range,e.g., from 12 to 100 percent, or from 20 to 90 percent or from 25 to 50percent.

In an alternate non-limiting embodiment, the photochromic article of thepresent invention is adapted to exhibit an unactivated state luminoustransmittance of greater than 70 percent at 23° C., an activated stateluminous transmittance at saturation less than 30 percent when activatedat 23° C. by simulated sunlight from a xenon arc lamp set at 6.7Watts/meter² UVA and 50,000 lumens/meter², and an activated stateluminous transmittance at saturation less than 60 percent when activatedat 28° C. by simulated sunlight from a xenon arc lamp through an UVblocking transparency rendering an irradiance integrated between 380 and420 nanometers of 0.75 Watts/meter² and 1,700 lumens/meter².

In another non-limiting embodiment, the photochromic article of thepresent invention is adapted to exhibit an unactivated state luminoustransmittance of greater than 80 percent at 23° C., an activated stateluminous transmittance at saturation less than 30 percent when activatedat 23° C. by simulated sunlight from a xenon arc lamp set at 6.7Watts/meter² UVA and 50,000 lumens/meter², and an activated stateluminous transmittance at saturation less than 40 percent when activatedat 28° C. by simulated sunlight from a xenon arc lamp through an UVblocking transparency rendering an irradiance integrated between 380 and420 nanometers of 0.75 Watts/meter² and 1,700 lumens/meter².

In the aforementioned alternate non-limiting embodiment, thephotochromic articles reach saturation within 15 to 30 minutes ofexposure to the simulated sunlight and/or simulated sunlight filtered bythe UV radiation blocking transparency at 23° C. and 28° C. The term“activated luminous state transmittance at saturation” means that thetransmittance of the photochromic article has reached a point where itwill not substantially change due to continued exposure to simulatedsunlight. Stated another way, the transmittance at saturation uponcontinued exposure to activating radiation does not vary by more than 5percent of the percent transmittance value.

The aforementioned unactivated state luminous transmittance at 23° C.can range between any of the aforestated values, e.g., from 70.1 to 100percent or from 80.1 to 100 percent, and their inclusive values, e.g.,from 71 to 99 percent or from 81 to 99 percent. The activated stateluminous transmittance at saturation when the photochromic article isactivated at 23° C. by simulated sunlight from a xenon arc lamp set at6.7 Watts/meter² UVA and 50,000 lumens/meter² can range between theaforestated values, e.g., from 29.9 to 0 percent, and their inclusivevalues, e.g., from 29 to 10 percent, or from 25 to 15 percent. Theactivated state luminous transmittance at saturation when thephotochromic article is activated at 28° C. by simulated sunlight from axenon arc lamp through an UV blocking transparency rendering anirradiance integrated between 380 and 420 nanometers of 0.75Watts/meter² and 1,700 lumens/meter². can range between any of theaforestated values, e.g., from 0 to less than 60 percent, e.g., 59.9percent, or from 0 to less than 40 percent e.g., 39.9 percent, and theirinclusive values, e.g., from 1 to 59 percent, or from 10 to 50 percentor from 15 to 40 percent.

The photochromic materials used to adapt the photochromic article foractivation behind ultraviolet radiation blocking transparencies arereferred to herein as Behind the Windshield photochromic materials orBWS photochromic materials.

The Behind the Windshield Test and the Outdoor Test are described inExample 13 herein. Basically, test samples containing BWS photochromicmaterials with or without other photochromic materials are tested forphotochromic response, e.g., the change in optical density, with thesimulated windshield in place under conditions simulating an eyeglasswearer behind an automotive windshield exposure (BWS) versus conditionssimulating outdoor exposure in the Outdoor Test (OS). The retainedoptical density is calculated by using the following formula:%ΔOD Retained=100×(ΔOD _(BWS) /ΔOD _(OS)).

In one non-limiting embodiment, the photochromic articles of the presentinvention are substantially free of ultraviolet absorbing materials inconcentrations that would substantially inhibit the activation of thephotochromic materials by radiation below 380 nanometers. In analternate non-limiting embodiment, the photochromic articles of thepresent invention do not contain ultraviolet absorbing materials inconcentrations that would prevent greater than 50 percent of theactivation of the photochromic materials, as measured by delta OD byradiation below 380 nanometers.

In a series of non-limiting embodiments, the BWS photochromic materialsof the present invention include photochromic materials adapted tochange from an unactivated form to an activated form by exposure toradiation substantially in the wavelength range from 380 to 410nanometers when measured over a range of from 380 to 700 nanometers.Classes of photochromic materials that can include BWS photochromicmaterials include naphthopyrans, benzopyrans, phenanthropyrans,indenonaphthopyrans, oxazines, metal-dithiozonates, fulgides,fulgimides, spiro(indoline)pyrans or mixtures thereof. In onenon-limiting embodiment, the BWS materials are chosen from thephotochromic materials represented by graphic formula XIII and mixturesthereof with the other photochromic materials. In the definitions of thesubstituents shown in formulae I to XIV, like symbols have the samemeaning unless stated otherwise.

In one non-limiting embodiment, a photochromic material is chosen from afluoranthenoxazine represented by the following graphic formula I:

wherein,

(a) R₁ is chosen from hydrogen, C₁–C₈ alkyl, C₃–C₇ cycloalkyl,phen(C₁–C₄)alkyl, naphth(C₁–C₄)alkyl, allyl, acrylyloxy(C₂–C₆)alkyl,methacrylyloxy(C₂–C₆)alkyl, C₂–C₄acyloxy (C₂–C₆)alkyl,carboxy(C₂–C₆)alkyl, cyano(C₂–C₆)alkyl, hydroxy(C₂–C₆)alkyl,triarylsilyl, triarylsilyloxy, tri(C₁–C₆)alkylsilyl,tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ aloxy)silyl,di(C₁–C₆)alkyl(C₁–C₆aloxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆alkyl)silyl,di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyloxy, C₁–C₆ alkoxy(C₂–C₄)alkyl or(C₂H₄O)_(r).CH₃, wherein r is an integer from 1 to 6;

(b) R₂ is chosen from C₁–C₅ alkyl, C₁–C₅ alkoxy, nitro, cyano, C₁–C₈alkoxycarbonyl, C₁–C₄ acyloxy, halo, C₁–C₄ monohaloalkyl or C₁–C₄polyhaloalkyl; said halo substituents being chloro, fluoro, iodo orbromo and q is 0, 1 or 2;

(c) R₃ and R₄ are each independently chosen from C₁–C₅ alkyl, benzyl,phenyl, mono- or di-substituted phenyl, said phenyl substituents beingC₁–C₅ alkyl or C₁–C₅ alkoxy; or R₃ and R₄ taken together form a groupchosen from a cyclic ring of from 5 to 8 carbon atoms which includes thespiro carbon atom; examples of such groups include norbornyl oradamantyl;

(d) R₅ is chosen from hydrogen, —CH₂Q and —C(O)W, wherein Q is halogen,hydroxy, benzoyloxy, C₁–C₆ alkoxy, triarylsilyl, triarylsilyloxy,tri(C₁–C₆)alkylsilyl, tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ aloxy)silyl,di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyl,di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyloxy, C₂–C₆ acyloxy, amino, C₁–C₆mono-alkylamino, C₁–C₆ dialkylamino, morpholino, piperidino,1-indolinyl, pyrrolidyl, or the group, —OCH(R₈)Z; W is the group,—OCH(R₈)Z, or an unsubstituted, mono-substituted, or di-substitutedheterocyclic ring containing 5 to 6 ring atoms, which ring includes asthe hetero atom a nitrogen atom alone or one additional hetero atom ofnitrogen or oxygen; examples of such heterocyclic rings include1-indolinyl, morpholino, piperidino, 1-pyrrolidyl, 1-imidazolidyl,2-imidazolin-1-yl, pyrazolidyl, pyrazolinyl or 1-piperazinyl; wherein Zis —CN, —CF₃, halogen, —C(O)R₈, or —COOR₈, R₈ is hydrogen or C₁–C₆alkyl; said heterocyclic ring substituents being chosen from C₁–C₆ alkylor C₁–C₆ alkoxy; or W is —OR₉ or —N(R₁₀)R₁₁, wherein R₉ is chosen fromhydrogen, allyl, C₁–C₆ alkyl, phenyl, mono(C₁–C₆)alkyl substitutedphenyl, mono(C₁–C₆)alkoxy-substituted phenyl, phenyl(C₁–C₃)alkyl,mono(C₁–C₆)alkyl substituted phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxysubstituted phenyl(C₁–C₃)alkyl, C₁–C₆ alkoxy(C₂–C₄)alkyl, or C₁–C₆haloalkyl; and R₁₀ and R₁₁ are each independently chosen from hydrogen,C₁–C₆ alkyl, C₅–C₇ cycloalkyl, phenyl, mono- or di-substituted phenyl,or R₁₀ and R₁₁ together with the nitrogen atom form a mono- ordi-substituted or unsubstituted heterocyclic ring containing from 5 to 6ring atoms, which ring includes as the hetero atom said nitrogen atomalone or one additional hetero atom of nitrogen or oxygen, said phenyland heterocyclic ring substituents being C₁–C₆ alkyl or C₁–C₆ alkoxy,and each of said halogen or halo groups in this part (d) being fluoro orchloro;

(e) each R₆ and R₇ is independently chosen for each occurrence fromaryl, mono(C₁–C₆)alkoxyaryl, di(C₁–C₆)alkoxyaryl, mono(C₁–C₆)alkylaryl,di(C₁–C₆)alkylaryl, bromoaryl, chloroaryl, fluoroaryl, C₃–C₇cycloalkylaryl, C₃–C₇ cycloalkyl, C₃–C₇ cycloalkyloxy, C₃–C₇cycloalkyloxy(C₁–C₆)alkyl, C₃–C₇ cycloalkyloxy(C₁–C₆)alkoxy,aryl(C₁–C₆)alkyl, aryl(C₁–C₆)alkoxy, aryloxy, aryloxy(C₁–C₆)alkyl,aryloxy(C₁–C₆)alkoxy, mono- or di(C₁–C₆)alkylaryl(C₁–C₆)alkyl, mono- ordi(C₁–C₆)alkoxyaryl(C₁–C₆)alkyl, mono- ordi(C₁–C₆)alkylaryl(C₁–C₆)alkoxy, mono- ordi(C₁–C₆)alkoxyaryl(C₁–C₆)alkoxy, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, diarylamino, N-(C₁–C₆)alkylpiperazino,N-arylpiperazino, aziridino, indolino, piperidino, arylpiperidino,morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino,pyrryl, C₁–C₆ alkyl, C₁–C₆ bromoalkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, C₁–C₆ alkoxy, mono(C₁–C₆)alkoxy(C₁–C₄)alkyl, acryloxy,methacryloxy, bromo, chloro or fluoro; and q is independently chosen foreach occurrence form the integer 0, 1, or 2.

In another non-limiting embodiment, the fluoranthenoxazine isrepresented by graphic formula I wherein:

(a) R₁ is chosen from C₁–C₈ alkyl, phen(C₁–C₄)alkyl,acrylyloxy(C₂–C₆)alkyl, methacrylyloxy(C₂–C₆)alkyl, carboxy(C₂–C₆)alkyl,tri(C₁–C₆)alkylsilyl, tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ aloxy)silyl,di(C₁–C₆)alkyl(C₁–C₆ aloxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆alkyl)silyl ordi(C₁–C₆)alkoxy(C₁–C₆alkyl)silyloxy;

(b) R₂ is chosen from C₁–C₅ alkyl, C₁–C₅ alkoxy, C₁–C₈ alkoxycarbonyl,C₁–C₄ acyloxy, halo, C₁–C₄ monohaloalkyl or C₁–C₄ polyhaloalkyl; saidhalo substituents being chloro or fluoro, and q is 0, 1 or 2;

(c) R₃ and R₄ are each independently chosen from C₁–C₅ alkyl, phenyl; orR₃ and R₄ taken together form a group chosen from a cyclic ring of from5 to 8 carbon atoms which includes the spiro carbon atom;

(d) R₅ is chosen from —CH₂Q and —C(O)W, wherein Q is halogen, hydroxy,C₁–C₆ alkoxy, tri(C₁–C₆)alkylsilyl, tri(C₁–C₆)alkylsilyloxy,tri(C₁–C₆)alkoxysilyl, tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆aloxy)silyl, di(C₁–C₆)alkyl(C₁–C₆ aloxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆alkyl)silyl, di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyloxy or the group,—OCH(R₈)Z; W is the group, —OCH(R₈)Z, morpholino or piperidino; Z is—COOR₈, R₈ is C₁–C₆ alkyl; or W is —OR₉ or —N(R₁₀)R₁₁, wherein R₉ ischosen from C₁–C₆ alkyl or phenyl; and R₁₀ and R₁₁ are eachindependently chosen from hydrogen, C₁–C₆ alkyl, or R₁₀ and R₁₁ togetherwith the nitrogen atom form a heterocyclic ring chosen from morpholinoor piperidino; and each of said halogen or halo groups in this part (d)being fluoro or chloro;

(e) each R₆ and R₇ is independently chosen for each occurrence fromaryl, mono(C₁–C₆)alkoxyaryl, di(C₁–C₆)alkylamino, piperidino,morpholino, C₁–C₆ alkoxy, or fluoro; and q is independently chosen foreach occurrence form the integer 0, 1, or 2.

In a further non-limiting embodiment, the fluoranthenoxazine representedby graphic formula I is chosen from:

-   (a)    1,3,3-trimethyl-spiro[indoline-2,5′-[3H]-fluorantheno[3,2-b][1,4]oxazine];-   (b) 1,3,3,4,5 (or    1,3,3,5,6)-pentamethyl-spiro[indoline-2,5′-[3H]-fluorantheno[3,2-b][1,4]oxazine];-   (c) 1-propyl-3,3,4,5 (or    3,3,5,6)-tetramethyl-spiro[indoline-2,5′-[3H]-fluorantheno[3,2-b][1,4]oxazine];-   (d)    1-methoxyethyl-3,3-dimethyl-spiro[indoline-2,5′-[3H]-fluorantheno[3,2-b][1,4]oxazine];    or-   (e) mixtures thereof.

The materials represented by graphic formula I can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. No. 5,808,063

In one non-limiting embodiment, a photochromic material is chosen from anaphthopyran represented by the following graphic formula II:

wherein:

(a) R₁₂ is hydrogen or a C₁–C₆ alkyl;

(b) R₁₃ is hydrogen or the group, —C(O)J, J being —OR₁₅ or —N(R₁₀)R₁₁,wherein R₁₅ is hydrogen, allyl, C₁–C₆ alkyl, phenyl, C₁–C₆ monoalkylsubstituted phenyl, C₁–C₆ monoalkoxy substituted phenyl,phenyl(C₁–C₃)alkyl, C₁–C₆ monoalkyl substituted phenyl(C₁–C₃)alkyl,C₁–C₆ monoalkoxy substituted phenyl(C₁–C₃)alkyl, C₁–C₆alkoxy(C₂–C₄)alkyl, or C₁–C₆ monohaloalkyl, and wherein R₁₀ and R₁₁ arethe same as described hereinbefore in (d) for the material representedby graphic formula I, and said halo substituent being chloro or fluoro;

(c) R₁₄ is —OR₉, —N(R₁₀)R₁₁, wherein R₉, R₁₀ and R₁₁ are the same asdescribed hereinbefore in (d) for the material represented by graphicformula I, or the group, —C(O)V; wherein V is C₁–C₆ alkyl, phenyl, C₁–C₆mono- or C₁–C₆ di-alkyl substituted phenyl, C₁–C₆ mono- or C₁–C₆di-alkoxy substituted phenyl, C₁–C₆ alkoxy, phenoxy, C₁–C₆ mono- orC₁–C₆ di-alkyl substituted phenoxy, C₁–C₆ mono- or C₁–C₆ di-alkoxysubstituted phenoxy, C₁–C₆ alkylamino, phenylamino, C₁–C₆ mono- or C₁–C₆di-alkyl substituted phenylamino, or C₁–C₆ mono- or C₁–C₆ di-alkoxysubstituted phenylamino, and said halo substituent being chloro, fluoroor bromo, provided that either R₁₂ or R₁₃ is hydrogen; and

(d) B and B′ are each independently chosen from:

-   -   (i) mono-T-substituted phenyl, wherein the group T is        represented by the formula:        -G[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′        —[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′        wherein -G being chosen from —C(O)— or —CH₂—, G′ being chosen        from C₁–C₃ alkoxy or a polymerizable group, x, y and z each        being independently chosen from a number between 0 and 50, and        the sum of x, y and z being between 2 and 50;    -   (ii) an unsubstituted, mono-, di-, or tri-substituted aryl        group, phenyl or naphthyl;    -   (iii) 9-julolidinyl or the unsubstituted, mono- or        di-substituted heteroaromatic group chosen from pyridyl furanyl,        benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl,        benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl,        benzopyridyl, indolinyl or fluorenyl, each of said aryl and        heteroaromatic substituents in (ii) and (iii) being        independently chosen from hydroxy, —C(O)U, wherein U being        hydroxy, C₁–C₆ alkyl, C₁–C₆ alkoxy, phenyl, mono-substituted        phenyl, amino, mono (C₁–C₆)alkylamino, di-(C₁–C₆)alkylamino,        morpholino, piperidino or pyrrolidyl; aryl,        mono(C₁–C₆)alkoxyaryl, di(C₁–C₆)alkoxyaryl,        mono(C₁–C₆)alkylaryl, di(C₁–C₆)alkylaryl, chloroaryl,        fluoroaryl, C₃–C₇ cycloalkylaryl, C₃–C₇ cycloalkyl, C₃–C₇        cycloalkyloxy, C₃–C₇ cycloalkyloxy(C₁–C₆)alkyl, C₃–C₇        cycloalkyloxy(C₁–C₆)alkoxy, aryl(C₁–C₆)alkyl, aryl(C₁–C₆)alkoxy,        aryloxy, aryloxy(C₁–C₆)alkyl, aryloxy(C₁–C₆)alkoxy, mono- or        di-(C₁–C₆)alkylaryl(C₁–C₆)alkyl, mono- or        di-(C₁–C₆)alkoxyaryl(C₁–C₆)alkyl, mono- or        di-(C₁–C₆)alkylaryl(C₁–C₆)alkoxy, mono- or        di-(C₁–C₆)alkoxyaryl(C₁–C₆)alkoxy, amino, mono(C₁–C₆)alkylamino,        di(C₁–C₆)alkylamino, diarylamino, piperazino,        N-(C₁–C₆)alkylpiperazino, N-arylpiperazino, aziridino, indolino,        piperidino, morpholino, thiomorpholino, tetrahydroquinolino,        tetrahydroisoquinolino, pyrrolidyl, C₁–C₆ alkyl, C₁–C₆        chloroalkyl, C₁–C₆ fluoroalkyl, C₁–C₆ alkoxy,        mono(C₁–C₆)alkoxy(C₁–C₄)alkyl, acryloxy, methacryloxy, bromo,        chloro or fluoro, said aryl being chosen from phenyl or        naphthyl;    -   (iv) an unsubstituted or mono-substituted group chosen from        pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolinyl,        phenothiazinyl, phenoxazinyl, phenazinyl or acridinyl, each of        said substituents being independently chosen from C₁–C₆ alkyl,        C₁–C₆ alkoxy, phenyl, fluoro, chloro or bromo;    -   (v) a monosubstituted phenyl, said phenyl having a substituent        located at the para position being a linking group, —(CH₂)_(r)—        or —O—(CH₂)_(r)—, connected to an aryl group which is a member        of another photochromic material, and r being chosen from the        integer 1, 2, 3, 4, 5 or 6;    -   (vi) a group represented by one of the following graphic        formulae:

wherein A being independently chosen in each formula from methylene oroxygen and D being independently chosen in each formula from oxygen orsubstituted nitrogen, provided that when D is substituted nitrogen, A ismethylene; said nitrogen substituents being chosen from hydrogen, C₁–C₆alkyl, or C₂–C₆ acyl; each R₂₀ being independently chosen for eachoccurrence in each formula from C₁–C₆ alkyl, C₁–C₆ alkoxy, hydroxy,chloro or fluoro; R₁₈ and R₁₉ each being independently chosen in eachformula from hydrogen or C₁–C₆ alkyl; and q being chosen from theinteger 0, 1 or 2;

-   -   (vii) C₁–C₆ alkyl, C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl, C₁–C₆        alkoxy(C₁–C₄)alkyl, C₃–C₆ cycloalkyl,        mono(C₁–C₆)alkoxy(C₃–C₆)cycloalkyl,        mono(C₁–C₆)alkyl(C₃–C₆)-cycloalkyl, chloro(C₃–C₆)cycloalkyl,        fluoro(C₃–C₆)cyclo-alkyl or C₄–C₁₂ bicycloalkyl;    -   (viii) a group represented by the following graphic formula:

wherein L being chosen from hydrogen or C₁–C₄ alkyl and M being chosenfrom an unsubstituted, mono-, or di-substituted group chosen fromnaphthyl, phenyl, furanyl, or thienyl; each of said group substituentsbeing independently chosen from C₁–C₄ alkyl, C₁–C₄ alkoxy, fluoro, orchloro; or

-   -   (ix) B and B′ taken together form fluoren-9-ylidene, mono-, or        di-substituted fluoren-9-ylidene or a group being independently        chosen from saturated C₃–C₁₂ spiro-monocyclic hydrocarbon rings,        saturated C₇–C₁₂ spiro-bicyclic hydrocarbon rings or saturated        C₇–C₁₂ spiro-tricyclic hydrocarbon rings; each of said        fluoren-9-ylidene substituents being independently chosen from        C₁–C₄ alkyl, C₁–C₄ alkoxy, fluoro or chloro.

In one non-limiting embodiment, when the T group is a substituent on thephotochromic materials as hereinbefore in (d) (i), polymerization of thephotochromic polymerizable compounds can occur by mechanisms describedin the definition of “polymerization” in Hawley's Condensed ChemicalDictionary, Thirteenth Edition, 1997, John Wiley & Sons, pages 901–902.Those mechanisms include by “addition”, in which free radicals are theinitiating agents that react with the double bond of the monomer byadding to it on one side at the same time producing a new free electronon the other side, by “condensation”, involving the splitting out ofwater molecules by two reacting monomers and by so-called “oxidativecoupling”. Non-limiting examples of the polymerizable groups arehydroxy, (meth)acryloxy, 2-(methacryloxy)ethylcarbamyl, or epoxy, e.g.,oxiranylmethyl. When there are 2 or more polymerizable groups on thenaphthopyran, they may be the same or different.

The group, —(OC₂H₄)_(x)—, in the group T formulae, can representpoly(ethylene oxide); —(OC₃H₆)_(y)—, can represent poly(propyleneoxide); and, (OC₄H₈)_(z)—, can represent poly(butylene oxide). When usedin combination, the poly(ethylene oxide), poly(propylene oxide) andpoly(butylene oxide) groups of T can be in a random or block orderwithin the T moiety. The letters x, y and z are each a number between 0and 50 and the sum of x, y and z is between 2 and 50. The sum of x, yand z can be any number that falls within the range of 2 to 50, e.g., 2,3, 4 . . . 50. This sum can also range from any lower number to anyhigher number within the range of 2 to 50, e.g., 6 to 50, 31 to 50. Thenumbers for x, y, and z are average values and can be partial numbers,e.g., 9.5.

In another non-limiting embodiment, the naphthopyran is represented bygraphic formula II wherein:

(a) R₁₂ is hydrogen;

(b) R₁₃ is hydrogen or the group, —C(O)J, J being —OR₁₅ or —N(R₁₀)R₁₁,wherein R₁₅ is C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, or C₁–C₆alkoxy(C₂–C₄)alkyl;

(c) R₁₄ is hydrogen, C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, C₁–C₆alkoxy(C₂–C₄)alkyl, C₅–C₇ cycloalkyl, or the group, —C(O)V; wherein V isC₁–C₆ alkyl, C₁–C₆ alkoxy or C₁–C₆ alkylamino; and

(d) B and B′ are each independently chosen from:

-   -   (i) an unsubstituted, mono-, di-, or tri-substituted phenyl        group;    -   (ii) a mono-substituted heteroaromatic group chosen from        benzofuran-2-yl, benzothien-3-yl, dibenzofuranyl, or carbazoyl;        each of said phenyl and heteroaromatic substituents in (i)        and (ii) being independently chosen from —C(O)U, wherein U being        C₁–C₆ alkyl, C₁–C₆ alkoxy, mono-(C₁–C₆)alkylamino,        di-(C₁–C₆)alkylamino, morpholino, or piperidino; or amino,        mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, piperidino,        morpholino or fluoro;    -   (iii) an unsubstituted or mono-substituted phenothiazinyl, said        substituents being C₁–C₆ alkyl or C₁–C₆ alkoxy;    -   (iv) a monosubstituted phenyl, said phenyl having a substituent        located at the para position being a linking group,        —O—(CH₂)_(r)—, connected to an aryl group which is a member of        another photochromic material, and r being chosen from the        integer 3 or 6;    -   (v) a group represented by one of the following graphic        formulae:

wherein A being independently chosen in each formula from methylene oroxygen and D being independently chosen in each formula from oxygen orsubstituted nitrogen, provided that when D is substituted nitrogen, A ismethylene; said nitrogen substituents being C₁–C₆ alkyl; each R₂₀ beingindependently chosen for each occurrence in each formula from C₁–C₆alkyl or C₁–C₆ alkoxy; R₁₈ and R₁₉ each being independently chosen ineach formula from hydrogen or C₁–C₆ alkyl; and q being chosen from theinteger 0, 1 or 2;

-   -   (vi) C₁–C₆ alkyl, C₃–C₆ cycloalkyl, or C₄–C₁₂ bicycloalkyl;    -   (vii) a group represented by the following graphic formula:

wherein L being hydrogen and M being an unsubstituted, mono-, ordi-substituted phenyl; each of said group substituents beingindependently chosen from C₁–C₄ alkoxy or fluoro; or

-   -   (viii) B and B′ taken together form fluoren-9-ylidene, mono-, or        di-substituted fluoren-9-ylidene or a saturated C₇–C₁₂        spiro-bicyclic hydrocarbon rings; each of said fluoren-9-ylidene        substituents being fluoro.

In further non-limiting embodiment, the naphthopyran represented bygraphic formula II is chosen from:

-   (a) 3,3-diphenyl-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;-   (b)    3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;-   (c)    3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;-   (d)    3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;-   (e) 3,3-diphenyl-8-methoxy-9-carbophenoxy-3H-naphtho[2,1-b]pyran;-   (f)    3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-methoxy-9-carbophenoxy-3H-naphtho[2,1-b]pyran;-   (g)    3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;-   (h)    3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;-   (i) 3,3-diphenyl-7-methyl-8-methoxy-3H-naphtho[2,1-b]pyran;-   (j)    3-(2-methoxy,4-acryloxyphenyl)-3-(4-methacryloxyphenyl)-8-benzyloxy-9-(carbo-1-indolinyl)-3H-naphtho[2,1-b]pyran;-   (k)    3-(2,4,6-trifluorophenyl)-3-(2,4,6-trimethoxy-1-naphthyl)-8-acetyl-9-carboniloyl-3H-naphtho[2,1-b]pyran;-   (l)    3-(2-fluorophenyl)-3-(3-methoxy-2-thienyl)-7-h-pentyl-8-benzoyloxy-3H-naphtho[2,1-b]pyran;-   (m)    3,3-spiroadamantylene-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;-   (n)    3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;-   (o)    3-(4-methoxyphenyl)-3-(2-phenyl-1-methylvinyl)-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;-   (p)    3-(4-methoxyphenyl)-3-(9-ethylcarbozol-2-yl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;-   (q)    3,3-spirofluoren-9-ylidene-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;-   (r) 3,3-diphenyl-8-morpholino-9-carbomethoxy-3H-naphtho[2,1-b]pyran;    or-   (s) mixtures thereof.

The materials represented by graphic formula II can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. Nos. 5,466,398, 5,578,252 and 5,637,262.

In one non-limiting embodiment, a photochromic material is chosen from anaphthopyran represented by the following graphic formula III:

wherein,

(a) R₂₁ is the group, —C(O)W or CH₂Q, described hereinbefore in (d) forthe material represented by graphic formula I;

(b) R₂₂ and each R₂₃ are independently chosen for each occurrence fromhydroxy, NH₂ or N(R)H; wherein R is C₁–C₆ alkyl or aryl and n is chosenfrom the integers 0, 1, 2, or 3; and

(c) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the naphthopyran is represented bygraphic formula III wherein:

(a) R₂₁ is the group, —C(O)W or CH₂Q, described hereinbefore in (d) forthe material represented by graphic formula I;

(b) R₂₂ and each R₂₃ are independently chosen for each occurrence fromhydroxy, NH₂ or N(R)H; wherein R is C₁–C₃ alkyl or phenyl and n ischosen from the integers 0, 1 or 2; and

(c) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In further non-limiting embodiment, the naphthopyran represented bygraphic formula III is chosen from:

-   (a)    2,2-di(4-methoxyphenyl)-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;-   (b)    2,2-di(4-methoxyphenyl)-5-methoxycarbonyl-6-amino-2H-naphtho[1,2,-b]pyran;-   (c)    2,2-di(4-methoxyphenyl)-5-methoxycarbonyl-6-propylamino-2H-naphtho[1,2-b]pyran;-   (d)    2-(4-methoxyphenyl)-2-t-butyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;-   (e)    2-(4-methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-amino-2H-naphtho[1,2-b]pyran;-   (f)    2,2-di(4-methylphenyl)-5-methoxycarbonyl-6-methylamino-2H-naphtho[1,2-b]pyran;-   (g) 2,2-diphenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;-   (h)    2,2-di(4-methoxyphenyl)-5-methoxycarbonyl-6-phenylamino-2H-naphtho[1,2-b]pyran;-   (i)    2,2-di(4-methoxyphenyl)-5-methoxycarbonyl-6-hydroxy-9-methoxy-2H-naphtho[1,2-b]pyran;-   (j)    2,2-diphenyl-5-methoxycarbonyl-6-phenylamino-2H-naphtho[1,2-b]pyran;-   (k)    2,2-di(3-trifluoromethylphenyl)-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;-   (l)    2-(4-methoxyphenyl)-2-(2-methyl,2,3-dihydrobenzofur-5-yl)-5-methoxycarbonyl-6-amino-2H-naphtho[l,2-b]pyran;-   (m)    2,2′-spiroadamantylene-5-methoxycarbonyl-6-methoxy-2H-naphtho[l,2-b]pyran;    or-   (n) mixtures thereof.

The materials represented by graphic formula III can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. Nos. 5,458,814; 5,573,712; 5,650,098; and 5,651,923.

In one non-limiting embodiment, a photochromic material is chosen from anaphthopyran represented by the following graphic formula IV:

wherein,

(a) R₅ is the same group described hereinbefore in (d) for the materialrepresented by graphic formula I;

(b) R₂₄ and R₂₅ are each chosen from hydrogen or an amino group definedhereinafter, provided that R₂₄ and R₂₅ are not both hydrogen; said aminogroup being:

-   -   (i) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each being independently chosen from        hydrogen, C₁–C₈ alkyl, aryl, furanyl, benzofuran-2-yl,        benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl,        dibenzofuranyl, dibenzothienyl, benzopyridyl, fluorenyl, C₁–C₈        alkylaryl, C₃–C₂₀ cycloalkyl, C₄–C₂₀ bicycloalkyl, C₅–C₂₀        tricycloalkyl or C₁–C₂₀ alkoxyalkyl and said aryl group being        phenyl or naphthyl;    -   (ii) a nitrogen containing ring represented by the following        graphic formula:

wherein each Y being independently chosen for each occurrence from—CH₂—, —CH(R₂₆)—, —C(R₂₆)(R₂₆)—, —CH(aryl)-, —C(aryl)₂— or —C(R₂₆)(aryl)-; X being —Y—, —O—, —S—, —S(O)—, —S(O₂)—, —NH—, —N(R₂₆)— or—N(aryl)-; R₂₆ being C₁–C₆ alkyl; said aryl group being phenyl ornaphthyl, m being chosen from the integer 1, 2 or 3 and p being chosenfrom the integer 0, 1, 2 or 3; provided that when p is 0, X is Y;

-   -   (iii) a group represented by one of the following graphic        formulae:

wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen, C₁–C₅ alkyl, phenyl ornaphthyl; or the groups R₂₈ and R₂₉ together form a ring of 5 to 8carbon atoms; R₂₇ being chosen independently for each occurrence fromC₁–C₆ alkyl, C₁–C₆ alkoxy, fluoro or chloro and q being chosen from theinteger 0, 1 or 2;

-   -   (iv) unsubstituted, mono- or di-substituted C₄–C₁₈ spirobicyclic        amine; or    -   (v) unsubstituted, mono- or di-substituted C₄–C₁₈ spirotricyclic        amine; said substituents for (iv) and (v) being independently        chosen for each occurrence from aryl, C₁–C₆ alkyl, C₁–₆ alkoxy        or phenyl(C₁–C₆)alkyl; and

(c) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the naphthopyran is represented bygraphic formula IV wherein:

(a) R₅ is chosen from the groups described hereinbefore in (d) for thematerial represented by graphic formula I;

(b) R₂₄ and R₂₅ are each chosen from hydrogen or an amino group definedhereinafter, provided that R₂₄ and R₂₅ are not both hydrogen; said aminogroup being:

-   -   (i) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each being independently chosen from        C₁–C₈ alkyl, aryl, or C₃–C₂₀ cycloalkyl; and said aryl group        being phenyl or naphthyl;    -   (ii) a nitrogen containing ring represented by the following        graphic formula:

wherein each Y being independently chosen for each occurrence from—CH₂—, ; X being —Y—, —O—, —S—, or —N(R₂₆)—; R₂₆ being C₁–C₆ alkyl; saidaryl group being phenyl or naphthyl, m being chosen from the integer 1,2 or 3 and p being chosen from the integer 0, 1, 2 or 3; provided thatwhen p is 0, X is Y; or

-   -   (iii) a group represented by one of the following graphic        formulae:

wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen; R₂₇ being chosen independentlyfor each occurrence from C₁–C₆ alkyl, and q being chosen from theinteger 0, 1 or 2; and

(c) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the naphthopyran represented bygraphic formula IV is chosen from:

-   (a)    2-phenyl-2-(4-morpholinophenyl)-5-carbomethoxy-9-dimethylamino-2H-naphtho[1,2-b]pyran;-   (b)    2,2-di(4-methoxyphenyl)-5-methoxymethyl-9-morpholino-2H-naphtho[1,2-b]pyran;-   (c)    2-(4-methoxyphenyl)-2-(4-piperidinophenyl)-5-carbomethoxy-9-dimethylamino-2H-naphtho[1,2-b]pyran;    or-   (d) mixtures thereof.

The materials represented by graphic formula IV can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. Nos. 6,248,264 and 6,348,604.

In one non-limiting embodiment, a photochromic material is chosen from aphenanthropyran represented by one of the following graphic formula VAor VB:

wherein,

(a) R₃₁ is the group R₅, described hereinbefore in (d) for the materialrepresented by graphic formula I;

(b) R₃₂ is hydrogen, C₁–C₆ alkyl, C₁–C₆ alkoxy, C₃–C₇ cycloalkyl,pyridyl, phenyl, mono-substituted or di-substituted phenyl, said phenylsubstituents being C₁–C₆ alkyl, C₁–C₆ alkoxy, hydroxy, amino, chloro, orfluoro;

(c) each R₃₃ is independently chosen for each occurrence from chloro,fluoro, amino, C₁–C₆ monoalkylamino, —N(R₁₀)R₁₁, as describedhereinbefore in (d) for the material represented by graphic formula I,phenyl, C₁–C₆ alkyl, or —OR₃₄, wherein R₃₄ is hydrogen, C₁–C₆ alkyl,allyl, or acetyl, and q is the integer 0, 1, or 2; and

(d) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the phenanthropyran is representedby graphic formula VA or VB wherein:

(a) R₃₁ is the group, R₅ described hereinbefore in (d) for the materialrepresented by graphic formula I;

(b) R₃₂ is hydrogen or C₁–C₆ alkyl;

(c) each R₃₃ is independently chosen for each occurrence from—N(R₁₀)R₁₁, which was described hereinbefore in (d) for the materialrepresented by graphic formula I, C₁–C₆ alkyl, or —OR₃₄, wherein R₃₄ isC₁–C₆ alkyl, and q is the integer 0, 1, or 2; and

(d) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the phenanthropyran represented bygraphic formula VA or VB is chosen from:

-   (a)    3,3-diphenyl-12-methoxycarbonyl-11-methyl-3H-phenanthro[1,2-b]pyran;-   (b)    2,2-diphenyl-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran;-   (c)    2-(4-methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran;-   (d)    3-(2-fluorophenyl)-3-(4-methoxyphenyl)-6-methoxy-12-methoxycarbonyl-3H-phenanthro[1,2-b]pyran;-   (e)    spiro[3H-6-methoxy-12-methoxycarbonylphenanthro[1,2-b]pyran-3-9′-fluorene];-   (f)    2,2-di(4-methoxyphenyl)-10-methoxy-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran;-   (g)    3-(2,3-dihydrobenzofur-5-yl)-3-(4-methoxyphenyl)-6-methoxy-12-methoxycarbonyl-11-methyl-3H-phenanthro[1,2-b]pyran;-   (h)    3,3-diphenyl-6-methoxy-12-methoxycarbonyl-11-phenyl-3H-phenanthro[1,2-b]pyran;-   (i)    3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-6-methoxy-12-methoxycarbonyl-11-phenyl-3H-phenanthro[1,2-b]pyran;-   (j)    3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-6-methoxy-12-hydroxymethyl-11-phenyl-3H-phenanthro[1,2-b]pyran;-   (k)    2,2-diphenyl-5-N,N-dimethylaminocarbonyl-2H-phenanthro[4,3-b]pyran;    or-   (l) mixtures thereof.

The materials represented by graphic formula V can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. No. 5,514,817.

In one non-limiting embodiment, a photochromic material is chosen from afluoranthenopyran represented by the following graphic formula VI:

wherein,

(a) R₃₅ and R₃₆ are each independently chosen for each occurrence fromhydroxy, aryl, mono(C₁–C₆)alkoxyaryl, di(C₁–C₆)alkoxyaryl,mono(C₁–C₆)alkylaryl, di(C₁–C₆)alkylaryl, bromoaryl, chloroaryl,fluoroaryl, C₃–C₇ cycloalkylaryl, C₃–C₇ cycloalkyl, C₃–C₇ cycloalkyloxy,C₃–C₇ cycloalkyloxy(C₁–C₆)alkyl, C₃–C₇ cycloalkyloxy(C₁–C₆)alkoxy,aryl(C₁–C₆)alkyl, aryl(C₁–C₆)alkoxy, aryloxy, aryloxy(C₁–C₆)alkyl,aryloxy(C₁–C₆)alkoxy, mono- or di(C₁–C₆)alkylaryl(C₁–C₆)alkyl, mono- ordi(C₁–C₆)alkoxyaryl(C₁–C₆)alkyl, mono- ordi(C₁–C₆)alkylaryl(C₁–C₆)alkoxy, mono- ordi(C₁–C₆)alkoxyaryl(C_(l)-C₆)alkoxy, C₁–C₆ alkyl, C₁–C₆ bromoalkyl,C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl, C₁–C₆ alkoxy,mono(C₁–C₆)alkoxy(C₁–C₄)alkyl, acryloxy, methacryloxy, bromo, chloro,fluoro, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, phenylamino,mono- or di-(C₁–C₆)alkyl substituted phenylamino or mono- ordi-(C₁–C₆)alkoxy substituted phenylamino, and q is the integer 0, 1 or2;

(b) R₅ is chosen from the group described hereinbefore in (d) for thematerial represented by graphic formula I; and

(c) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the fluoranthenopyran is representedby graphic formula VI wherein:

(a) R₃₅ and R₃₆ are each independently chosen for each occurrence fromC₁–C₆ alkyl, C₁–C₆ alkoxy, fluoro, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, phenylamino, mono- or di-(C₁–C₆)alkyl substitutedphenylamino or mono- or di-(C₁–C₆)alkoxy substituted phenylamino, and qis the integer 0, 1 or 2;

(b) R₅ is chosen from the group described hereinbefore in (d) for thematerial represented by graphic formula I; and

(c) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the fluoranthenopyran representedby graphic formula VI is chosen from:

-   (a)    5,5-bis(4-methoxyphenyl)-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran;-   (b)    5-(4-methoxyphenyl)-5-(4-morpholinophenyl)-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran;-   (c) 5,5-diphenyl-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran;-   (d) 5,5-bis(4-methoxyphenyl)-8-methylol-5H-fluorantheno[3,2-b]pyran;-   (e)    5,5-bis(4-methoxyphenyl)-2-methoxy-8-methoxycarbonyl-5H-fluorantheno[3,2-b]pyran;    or-   (f) mixtures thereof.

The materials represented by graphic formula VI can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. No. 5,891,368.

In one non-limiting embodiment, a photochromic material is chosen from anaphthopyran represented by the following graphic formula VII:

wherein,

(a) R₃₇ and R₃₈ together form an oxo group or R₃₇ and R₃₈ each areindependently chosen for each occurrence from hydrogen, C₁–C₆ alkyl,C₃–C₇ cycloalkyl, allyl, phenyl, mono- or di-substituted phenyl, benzyl,mono-substituted benzyl, naphthyl, mono- or di-substituted naphthyl,C₄–C₁₂ bicycloalkyl, linear or branched C₃–C₁₂ alkenyl, C₁–C₆ alkoxycarbonyl(C₁–C₆)alkyl, methacryloxy(C₁–C₆)alkyl, acryloxy(C₁–C₆)alkyl,C₁–C₄ acyloxy(C₁–C₆)alkyl, C₁–C₆ alkoxy(C₁–C₆)alkyl or theunsubstituted, mono- or di-substituted heteroaromatic groups pyridyl,furanyl, benzofuran-2-yl, benzyfuran-3-yl, thienyl, benzothien-2-yl,benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazolyl,benzopyridyl and indolyl, each of said phenyl, benzyl, naphthyl andheteroaromatic group substituents being C₁–C₆ alkyl, C₁–C₆ alkoxy,morpholino, di(C₁–C₆)alkylamino, chloro or fluoro;

(b) R₃₉ is chosen from C₁–C₆ alkyl, C₁–C₆ alkoxy, chloro, fluoro,phenyl, mono- and di-substituted phenyl, benzyl or mono-substitutedbenzyl, C₃–C₇ cycloalkyl, aryloxy, di(C₁–C₆)alkylamino, morpholino,thiomorpholino, piperidino, pyridyl, tetrahydroquinolino, isoquinolino,aziridino, diarylamino, N-(C₁–C₆)alkyl piperizino or N-aryl piperizino,wherein the aryl groups are phenyl or naphthyl, each of said phenyl andbenzyl substituents being C₁–C₆ alkyl, C₁–C₆ alkoxy, fluoro or chloro,and q is the integer 0, 1 or 2;

(c) I is oxygen or —N(R₄₀)—, wherein R₄₀ is hydrogen C₁–C₆ alkyl, C₃–C₇cycloalkyl, allyl, vinyl, C₁–C₅ acyl, phenyl, mono- and di-substitutedphenyl, benzyl, mono-substituted benzyl, C₁–C₄alkoxycarbonyl(C₁–C₆)alkyl, methacryloxy(C₁–C₆)alkyl,acryloyloxy(C₁–C₆)alkyl, phenyl(C₁–C₆)alkyl, naphthyl, C₄–C₁₂bicycloalkyl, C₂–C₄ acyloxy or the unsubstituted or substitutedheteroaromatic groups pyridyl, furanyl, benzofuran-2-yl,benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl,dibenzofuranyl, dibenzothienyl, carbazolyl, benzopyridyl or indolyl,each of said phenyl, benzyl and heteroaromatic group substituents beingC₁–C₆ alkyl or C₁–C₆ alkoxy;

(d) K is oxygen, —N(R₄₀)— or —C(R₄₁)(R₄₂)—, wherein R₄₁ and R₄₂ are eachhydrogen, C₁–C₆ alkyl or C₃–C₇ cycloalkyl; and

(e) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the naphthopyran is represented bygraphic formula VII wherein:

(a) R₃₇ and R₃₈ together form an oxo group or R₃₇ and R₃₈ each areindependently chosen for each occurrence from hydrogen, C₁–C₆ alkyl,C₃–C₇ cycloalkyl, phenyl or methacryloxy(C₁–C₆)alkyl;

(b) R₃₉ is chosen from C₁–C₆ alkyl, C₁–C₆ alkoxy, fluoro, or morpholino,and q is the integer 0, 1 or 2;

(c) I is oxygen or —N(R₄₀)—, wherein R₄₀ is C₁–C₆ alkyl, C₃–C₇cycloalkyl or phenyl;

(d) K is oxygen, —N(R₄₀)— or —C(R₄₁)(R₄₂)—, wherein R₄₁ and R₄₂ are eachhydrogen or C₁–C₆ alkyl; and

(e) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the naphthopyran represented bygraphic formula VII is chosen from:

-   a)    7,7-diphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;-   b) 7,7-di(4-methoxyphenyl)-4-oxo-4H-7H-[1,3]dioxino    [5′,4′:3,4]naphtho[1,2-b]pyran;-   c)    7-(4-methoxyphenyl)-7-phenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;-   d) 7,7-diphenyl-2-ethyl-4-oxo-4H-7H-[1,3]dioxino    [5′,4′:3,4]naphtho[1,2-b]pyran;-   e) 7,7-diphenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino    [5′,4′:3,4]naphtho[1,2-b]pyran;-   f)    7,7-diphenyl-2-(2-methylpropyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;-   g) 2,7,7-triphenyl-4-oxo-4H-7H-[1,3]dioxino    [5′,4′:3,4]naphtho[1,2-b]pyran;-   h)    7,7-diphenyl-2-(1-phenylethyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;-   i) 3-methyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro    [1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;-   j)    3-(2-ethoxycarbonylethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;-   k)    3-hexyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;-   l)    3-(2-methacryloyloxyethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;-   m)    2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-pyrimidino[5′,4′:3,4]naphtho[1,2-b]pyran;-   n)    2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-[1,3]oxazino[5′,4′:3,4]naphtho[1,2-b]pyran;-   o)    7,7-diphenyl-1,2,4,7-tetrahydro-2,2-dimethylpyrano[3′,4′:3,4]naphtho[1,2-b]pyran;-   p)    7-phenyl-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;-   q)    7-(2-fluorophenyl)-7-(3-methyl-4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;-   r)    7-(4-methoxyphenyl)-7-(2,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;-   s)    7-(4-morpholino-2-fluorophenyl)-7-(4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;-   t)    7-(2-fluoro-4-methoxyphenyl)-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;-   u)    7-(4-morpholino-2-fluorophenyl)-7-(3,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;    or-   v) mixtures thereof.

The materials represented by graphic formula VII can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. No. 6,022,497.

In one non-limiting embodiment, a photochromic material is chosen from anaphthopyran represented by the following graphic formula VIII:

wherein,

(a) R₄₃ and R₄₄ together form an oxo group or R₄₃ and R₄₄ are bothhydrogen, C₁–C₆ alkyl, C₃–C₇ cycloalkyl, allyl, phenyl, mono-substitutedphenyl, benzyl or mono-substituted benzyl each of said phenyl and benzylgroup substituents being C₁–C₆ alkyl or C₁–C₆ alkoxy;

(b) R₄₅ is hydrogen, C₁–C₆ alkyl, C₃–C₇ cycloalkyl, or the group,CH(B)B′, wherein B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II;

(c) R₄₆ is hydrogen, C₁–C₆ alkyl, or C₃–C₇ cycloalkyl;

(d) each R₄₇ is C₁–C₆ alkyl, C₁–C₆ alkoxy, chloro or fluoro, and q isthe integer 0, 1, or 2; and

(e) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the naphthopyran is represented bygraphic formula VIII wherein:

(a) R₄₃ and R₄₄ together form an oxo group or R₄₃ and R₄₄ are bothhydrogen, C₁–C₆ alkyl, C₃–C₇ cycloalkyl or phenyl;

(b) R₄₅ is hydrogen or C₁–C₆ alkyl;

(c) R₄₆ is hydrogen or C₁–C₆ alkyl, C₃–C₇ cycloalkyl;

(d) each R₄₇ is C₁–C₆ alkyl, C₁–C₆ alkoxy or fluoro, and q is theinteger 0, 1 or 2; and

(e) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the naphthopyran represented bygraphic formula VIII is chosen from:

-   (a)    7,7-diphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;-   2-(4-methoxyphenyl)-2-(2,4-dimethoxy-phenyl)-7-diphenylmethyl-10-methyl-5-oxo-2H-5H-pyrano[3′,4′:3,4]naphtho[1,2-b]pyran.

The materials represented by graphic formula VIII can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. No. 6,106,744.

In one non-limiting embodiment, a photochromic material is chosen from anaphthopyran represented by the following graphic formulae IXA, IXB,IXC, IXD, IXE, IXF, IXG or IXH:

wherein,

(a) R₄₃ and R₄₄ are the same groups described hereinbefore in (a) forthe represented by graphic formula VIII;

(b) each R₄₇ and q are the same as described hereinbefore in (d) for thematerial represented by graphic formula VIII; and

(c) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the naphthopyran is represented bygraphic formulae IXA, IXB, IXC, IXD, IXE, IXF, IXG or IXH wherein:

(a) R₄₃ and R₄₄ are the same groups described hereinbefore in (a) forthe material represented by graphic formula VIII;

(b) each R₄₇ and q are the same as described hereinbefore in (d) for thematerial represented by graphic formula VIII; and

(c) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the naphthopyran represented bygraphic formula IXA, IXB, IXC or IXD is chosen from:

-   a)    2,2-bis(4-methoxyphenyl)-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;-   b)    6,6-bis(4-methoxyphenyl)-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;-   c)    6,6-bis(4-methoxyphenyl)-6,10-dihydro[2]benzopyrano-[3′,4′:3,4]naphtho(1,2-b)pyran;-   d)    2-(4-methoxyphenyl)-2-(4-morpholinophenyl)-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;-   e)    6-(4-methoxyphenyl)-6-(4-morpholinophenyl)-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;-   f)    10,10-dimethyl-6-(4-methoxyphenyl)-6-(4-morpholinophenyl)-6,10-dihydro[2]benzopyrano[3′,4′:3,4]-naphtho    (1,2-b) pyran;-   g)    2-(4-morpholinophenyl)-2-phenyl-10-oxo-2,10-dihydro-[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;-   h)    6-(4-morpholinophenyl)-6-phenyl-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;-   i)    2,2-bis(4-methoxyphenyl)-12,13-dimethoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;-   j)    6,6-bis(4-methoxyphenyl)-12,13-dimethoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;-   k)    6-(4-methoxyphenyl)-6-phenyl-12,13-dimethoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)-pyran;-   l)    2-(4-methoxyphenyl)-2-phenyl-12,13-dimethoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)    pyran;-   m)    6-(4-methoxyphenyl)-6-phenyl-12,13-dimethoxy-10,10-dimethyl-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;-   n)    2,2-bis(4-methoxphenyl)-12-methoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;-   o)    6,6-bis(4-methoxyphenyl)-12-methoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;-   p) 6,6-diphenyl-9-oxo-6,9-dihydro[1]benzopyrano    [3′,4′:3,4]naphtho(1,2-b)pyran;-   q)    3,3-diphenyl-8-oxo-3,8-dihydro[2]benzopyrano[3′,4′:5,6]naphtho(2,1-b)pyran;    or-   r) mixtures thereof.

The materials represented by graphic formula IXA, IXB, IXC, IXD, IXE,IXF, IXG or IXH can be produced by methods known to those skilled in theart, for example, as disclosed in U.S. Pat. Nos. 6,022,495 and6,149,841.

In one non-limiting embodiment, a photochromic material is chosen from anaphthopyran represented by the following graphic formulae XA or XB:

wherein,

(a) A′ is chosen from:

-   -   (i) an unsubstituted, mono-substituted or di-substituted        heterocyclic ring chosen from benzothieno, benzofurano or        indolo, the 2,3 or 3,2 positions of said heterocyclic ring being        fused to the i, j or k side of said naphthopyran represented by        graphic formula XA or said heterocyclic ring is fused to the f        side of said naphthopyran represented by graphic formula XB; or    -   (ii) an unsubstituted, mono-substituted or di-substituted indeno        group fused to the i, j or k side of said naphthopyran        represented by graphic formula XA or to the f side of said        naphthopyran represented by graphic formula XB; each of said        heterocyclic ring and indeno group substituents being C₁–C₆        alkyl, C₅–C₇ cycloalkyl, C₁–C₆ alkoxy, —N(R₁₀)R₁₁, which was        described hereinbefore in (d) for the material represented by        graphic formula I, chloro, fluoro, benzo, mono- or        di-substituted benzo group fused to the benzo portion of the        benzothieno, benzofurano, indeno or indolo moiety, said benzo        substitutent being C₁–C₆ alkyl, C₅–C₇ cycloalkyl, C₁–C₆ alkyl        mono-substituted (C₅–C₇)cycloalkyl, C₁–C₆ alkoxy, —N(R₁₀)R₁₁,        chloro or fluoro;

(b) R₄₈ is chosen from:

-   -   (i) —C(O)W′, W′ being —OR₉ or —N(R₁₀)R₁₁, which groups were        described hereinbefore in (d) for the material represented by        graphic formula I; or    -   (ii) —C(R₅₁)₂X′, wherein X′ is —CN, chloro, fluoro, hydroxy,        benzoyloxy, C₁–C₆ alkoxy, C₂–C₆ acyloxy, amino, C₁–C₆        mono-alkylamino, C₁–C₆ dialkylamino, morpholino, piperidino,        1-indolinyl, pyrrolidyl, or trimethylsilyloxy, R₅₁ is hydrogen,        C₁–C₆ alkyl, phenyl or naphthyl, and each of said phenyl and        heterocyclic ring substituents in this part (b) being C₁–C₆        alkyl or C₁–C₆ alkoxy;

(c) R₄₉ is hydrogen, C₁–C₆ alkyl, the mono-, di- or tri-substituted arylgroups phenyl or naphthyl, said aryl substituents being C₁–C₆ alkyl,C₁–C₆ alkoxy, chloro or fluoro; or

(d) each R₅₀ is chloro, fluoro, C₁–C₆ alkyl, C₁–C₆ alkoxy, phenyl,naphthyl, phenoxy, naphthoxy or the group, —N(R₁₀)R₁₁, which wasdescribed hereinbefore in (d) for the material represented by graphicformula I, and q is selected from the integers 0, 1 or 2 in saidnaphthopyran represented by graphic XA, or each R₅₀ is chloro, fluoro,phenoxy, naphthoxy or the group, —N(R₁₀)R₁₁, and p is selected from theintegers 0, 1, 2 or 3 in said naphthopyran represented by graphicformula XB; and

(e) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the naphthopyran is represented bygraphic formulae XA or XB wherein:

(a) A′ is chosen from:

-   -   (i) an unsubstituted, mono- or di-substituted heterocyclic ring;        and    -   (ii) an unsubstituted or mono-substituted indeno group, each of        said heterocyclic ring and indeno group substituents being C₁–C₄        alkyl, C₁–C₃ alkoxy, —N(R₁₀)R₁₁, which was described        hereinbefore in (d) for the material represented by graphic        formula I, benzo, mono- or di-substituted benzo group fused to        the indeno moiety, said benzo substitutents being C₁–C₃ alkyl,        C₁–C₃ alkoxy or —N(R₁₀)R₁₁;

(b) R₄₈ is chosen from:

-   -   (i) —C(O)W′, W′ being —OR₉ or —N(R₁₀)R₁₁, wherein said groups        were described hereinbefore in (d) for the material represented        by graphic formula I; or    -   (ii) —C(R₅₁)₂X′, wherein X′ is —CN, halogen, hydroxy,        benzoyloxy, C₁–C₄ alkoxy, C₂–C₄ acyloxy, amino, C₁–C₄        mono-alkylamino, C₁–C₄ dialkylamino, morpholino, piperidino,        1-indolinyl or pyrrolidyl, and R₅₁ is hydrogen, C₁–C₄ alkyl,        phenyl or naphthyl;

(c) R₄₉ is hydrogen, C₁–C₄ alkyl, the mono- or di-substituted arylgroups phenyl or naphthyl, said aryl substituents being C₁–C₄ alkyl orC₁–C₄ alkoxy, chloro or fluoro;

(d) each R₅₀ is fluoro, C₁–C₄ alkyl, C₁–C₄ alkoxy, phenyl, naphthyl,phenoxy, naphthoxy, or the group, —N(R₁₀)R₁₁, which was describedhereinbefore in (d) for the material represented by graphic formula I,and q is selected from the integers 0, 1 or 2 for the naphthopyranrepresented by graphic formula XA or p is selected from the integers 0,1, 2 or 3 for the naphthopyran represented by graphic formula XB; and

(e) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the naphthopyran represented bygraphic formula XA or XB is chosen from:

-   (a)    2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[12-b]pyran;-   (b)    2-(4-methoxyphenyl)-2-(4-propoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[12-b]pyran;-   (c)    2,2′-Spiroadamantylene-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[1,2-b]pyran;-   (d)    3,3-Bis(4-methoxyphenyl)-10-methoxy-3H-naphtho[2″,1″:4′,5′]furo[2′,3′:3,4]naphtho[1,2-b]pyran;-   (e)    3,3-Bis(4-methoxyphenyl)-3H-naphtho[1″,2″:4′,5′]furo[3′,2′:3,4]naphtho[1,2-b]pyran;-   (f)    3,3′-Spiroadamantylene-3H-naphtho[1″,2″:4′,5′]furo[3′,2′:3,4]naphtho[1,2-b]pyran;-   (g)    2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-indeno[3′,2′:7:8]naphtho[1,2-b]pyran;-   (h)    3,3-di(4-methoxyphenyl)-6,11-dimethoxy-13-butyl-13-ethoxy-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;-   (i)    3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;    or-   (j) mixtures thereof.

The materials represented by graphic formula XA or XB can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. No. 5,651,923.

In one non-limiting embodiment, a photochromic material is chosen from aindenonaphthopyran represented by the following graphic formulae XIA orXIB:

wherein,

(a) A″ is an unsubstituted, mono-substituted or di-substitutedheterocyclic ring chosen from furo, thieno, benzothieno, benzofurano andindolo, the 2,3 or 3,2 positions of said heterocyclic ring being fusedto the g, h, i, n, o or p side of said indenonaphthopyran, saidheterocyclic ring substituents being C₁–C₆ alkyl, C₅–C₇ cycloalkyl,C₁–C₆ alkoxy, chloro or fluoro;

(b) R₅₂ and R₅₃ together form an oxo group, a spiro heterocyclic grouphaving 2 oxygen atoms and from 3 to 6 carbon atoms including thespirocarbon atom, or R₅₂ and R₅₃ are each hydrogen, hydroxy, C₁–C₆alkyl, C₃–C₇ cycloalkyl, allyl, phenyl, mono-substituted phenyl, benzyl,mono-substituted benzyl, chloro, fluoro or the group, —C(O)W″, whereineach W″ is hydroxy, C₁–C₆ alkyl, C₁–C₆ alkoxy, phenyl, mono-substitutedphenyl, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, morpholino,piperidino or pyrrolidyl; or R₅₂ and R₅₃ are each the group, the group,—N(R₁₀)R₁₁, as described hereinbefore in (d) for the materialrepresented by graphic formula I, or —OR₅₄, wherein each R₅₄ is C₁–C₆alkyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl,C₁–C₆ alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl, mono(C₁–C₄)alkyl substitutedC₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl, allyl, thegroup, —CH(R₅₅)X″, wherein each R₅₅ is hydrogen or C₁–C₃ alkyl, each X″is —CN, —CF₃, or —COOR₅₅, or each R₅₄ is the group, —C(O)Y′, whereineach Y′ is hydrogen, C₁–C₆ alkyl, C₁–C₆ alkoxy, the unsubstituted, mono-or di-substituted aryl groups, phenyl and naphthyl, phenoxy, mono- ordi-(C₁–C₆)alkyl substituted phenoxy, mono- or di-(C₁–C₆)alkoxysubstituted phenoxy, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino,phenylamino, mono- or di-(C₁–C₆)alkyl substituted phenylamino or mono-or di-(C₁–C₆)alkoxy substituted phenylamino, each of said phenyl, benzyland aryl group substituents being C₁–C₆ alkyl or C₁–C₆ alkoxy;

(c) each R₄₇ and q are the same as described hereinbefore in (d) for thematerial represented by graphic formula VIII; and

(d) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the naphthopyran is represented bygraphic formulae XIA or XIB wherein:

(a) A″ is an unsubstituted, mono-substituted or di-substitutedheterocyclic ring chosen from furo, thieno, benzothieno, benzofurano orindolo, the 2,3 or 3,2 positions of said heterocyclic ring being fusedto the p side of said indenonaphthopyran, said heterocyclic ringsubstituents being C₁–C₆ alkyl;

(b) R₅₂ and R₅₃ together form an oxo group, a spiro heterocyclic grouphaving 2 oxygen atoms and from 3 to 6 carbon atoms including thespirocarbon atom, or R₅₂ and R₅₃ are each hydrogen, hydroxy, C₁–C₆alkyl, C₃–C₇ cycloalkyl, phenyl or the group, —C(O)W″, wherein each W″is C₁–C₆ alkoxy, mono(C₁–C₆)alkylamino or di(C₁–C₆)alkylamino, or R₅₂and R₅₃ are each the group, —N(R₁₀)R₁₁, as described hereinbefore in (d)for the material represented by graphic formula I, or —OR₅₄, whereineach R₅₄ is C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, the group, —CH(R₅₅)X″,wherein each R₅₅ is hydrogen or C₁–C₃ alkyl, each X″ is —COOR₅₅, or eachR₅₄ is the group, —C(O)Y′, wherein each Y′ is C₁–C₆ alkyl;

-   -   (c) each R₄₇ and q are the same as described hereinbefore in (d)        for the material represented by graphic formula VIII; and

(d) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the naphthopyran represented bygraphic formula XIA or XIB is chosen from:

-   (a)    3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;-   (b)    3,3-di(4-methoxyphenyl)-16-hydroxy-16H-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;-   (c)    3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;    or-   (d) mixtures thereof.

The materials represented by graphic formula XIA or XIB can be producedby methods known to those skilled in the art, for example, as disclosedin U.S. Pat. No. 5,698,141.

In one non-limiting embodiment, a photochromic material is chosen froman indenonaphthopyran represented by graphic formulae XIIA or XIIBwherein:

(a) A″ is the same as described hereinbefore in (a) for the materialrepresented by graphic formula XIA or XIB;

(b) R₅₆ is hydrogen, hydroxy, bromo, fluoro or chloro and R₅₇ is thegroup, —CH(V′)₂, wherein V′ is —CN or —COOR₅₈, and each R₅₈ is hydrogen,C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl orthe unsubstituted, mono- or di-substituted aryl groups phenyl ornaphthyl, or R₅₇ is the group, —CH(R₅₉)Y″, wherein R₅₉ is hydrogen,C₁–C₆ alkyl or the unsubstituted, mono- or di-substituted aryl groupsphenyl or naphthyl, and Y″ is —COOR₅₈, —COR₅₉, or —CH₂OR₆₀, wherein R₅₉is hydrogen, C₁–C₆ alkyl, the unsubstituted, mono- or di-substitutedaryl groups phenyl or naphthyl, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, phenylamino, mono- or di-(C₁–C₆)alkyl substitutedphenylamino, mono- or di-(C₁–C₆)alkoxy substituted phenylamino,diphenylamino, mono- or di-(C₁–C₆)alkyl substituted diphenylamino, mono-or di-(C₁–C₆)alkoxy substituted diphenylamino, morpholino, orpiperidino; R₆₀ is hydrogen, —COR₅₈, C₁–C₆ alkyl, C₁–C₃alkoxy(C₁–C₆)alkyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl, orthe unsubstituted, mono- or di-substituted aryl groups phenyl ornaphthyl, each of said aryl group substituents being C₁–C₆ alkyl orC₁–C₆ alkoxy; or

(c) R₅₆ and R₅₇ together form the group, ═C(V′)₂ or ═C(R₅₉)W′″, whereinW′″ is —COOR₅₈ or —COR₅₉;

(d) each R₄₇ and q are the same as described hereinbefore in (d) for thematerial represented by graphic formula VIII; and

(e) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the naphthopyran is represented bygraphic formulae XIIA or XIIB wherein:

(a) A″ is the same as described hereinbefore in (a) for the materialrepresented by graphic formula XIA or XIB;

(b) R₅₆ is hydrogen or hydroxy and R₅₇ is the group, —CH(V′)₂, whereinV′ is —COOR₅₈, and each R₅₈ is C₁–C₆ alkyl or phenyl(C₁–C₃)alkyl; or R₅₇is the group, —CH(R₅₉)Y″, wherein R₅₉ is hydrogen and Y″ is —COOR₅₈, or—CH₂OR₆₀ wherein R₅₉ is C₁–C₆ alkyl or di(C₁–C₆)alkylamino; and R₆₀ isC₁–C₆ alkyl; or

(c) R₅₆ and R₅₇ together form the group, ═C(R₅₉)W′″, wherein W′″ is—COOR₅₈;

(d) each R₄₇ and q are the same as described hereinbefore in (d) for thematerial represented by graphic formula VIII; and

(e) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the naphthopyran represented bygraphic formula XIIA or XIIB is chosen from:

-   (a) 3,3-di(4-methoxyphenyl)-16-(ethoxycarbonyl)    methyl-16-hydroxy-3,16-di[H]-benzofuro[2′,3′:7,8]indeno    [2′,3′:3,4]naphtho[1,2-b]pyran;-   (b)    3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro    [2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;-   (c)    3-phenyl-3-(4-methoxyphenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro    [2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[l,2-b]pyran;-   (d)    3-phenyl-3-(4-morpholinophenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro    [2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran; or-   (e) mixtures thereof.

The materials represented by graphic formula XIIA or XIIB can beproduced by methods known to those skilled in the art, for example, asdisclosed in U.S. Pat. No. 5,723,072.

In one non-limiting embodiment, the Behind The Windshield (BWS)photochromic material is chosen from an indenonaphthopyran representedby the following graphic formula XIII:

wherein,

(a) R₆₁ is represented by:

-   -   (i) —SR₆₇, R₆₇ being chosen from C₁–C₆ alkyl, aryl, mono- or        di-substituted aryl, said aryl group being phenyl or naphthyl        and each of said aryl substituents being chosen independently        from C₁–C₆ alkyl, C₁–C₆ alkoxy or halogen;    -   (ii) an amino group described hereinbefore in (b) (i),        (ii), (iii) (iv) or (v) for the material represented by graphic        formula IV;

(b) R61′is independently chosen for each occurrence from C₁–C₆ alkyl orC₁–C₆ alkoxy and q being chosen from the integer 0, 1 or 2;

(c) R₆₂ and R₆₃ are each independently chosen from:

-   -   (i) hydrogen, hydroxy, amino, mono- or di-substituted amino,        C₁–C₁₂ alkyl, C₃–C₁₂ alkylidene, C₂–C₁₂ alkylidyne, vinyl, C₃–C₇        cycloalkyl, C₁–C₆ alkoxyalkyl, allyl, benzyl, mono-substituted        benzyl, chloro, fluoro or -C(O)W″, wherein W″ being the same        group described hereinbefore in (b) for the material represented        by graphic formula XIA or XIB; said amino substituents        in (c) (i) being C₁–C₆ alkyl, phenyl, benzyl or naphthyl; each        of said benzyl substituents being C₁–C₆ alkyl or C₁-C₆ alkoxy;    -   (ii) an unsubstituted, mono- di- or tri-substituted group chosen        from phenyl, naphthyl, phenanthryl, pyrenyl, quinolyl,        isoquinolyl, benzofuranyl, thienyl, benzothienyl,        dibenzofuranyl, dibenzothienyl, carbazolyl or indolyl; each of        said group substituents in (c) (ii) being chosen independently        for each occurrence from chioro, fluoro, C₁–C₆ alkyl or C₁–C₆        alkoxy;    -   (iii) a monosubstituted phenyl, said phenyl having a substituent        located at the para position being as described hereinbefore        in (d) (v) for the material represented by graphic formula II;    -   (iv) OR_(67′), R_(67′) being chosen from C₁–C₆ alkyl, C₁–C₆        acyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substituted        phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted        phenyl(C₁–C₃)alkyl, C₁–C₆ alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl,        mono(C₁–C₄)alkyl substituted C₃–C₇ cycloalkyl, C₁–C₆        chloroalkyl, C₁–C₆ fluoroalkyl, allyl, tri(C₁–C₆)alkylsilyl,        tri(C₁–C₆)alkoxysilyl, di(C₁–C₆)alkyl (C₁–C₆)alkoxysilyl,        di(C₁–C₆)alkoxy(C₁–C₆)alkylsilyl, benzoyl, mono-substituted        benzoyl, naphthoyl or mono-substituted naphthoyl; each of said        benzoyl and naphthoyl substituents being independently chosen        from C₁–C₆ alkyl or C₁–C₆ alkoxy; or R_(67′) being —CH(R₆₈)Q″,        wherein R₆₈ being chosen from hydrogen or C₁–C₃ alkyl and Q″        being chosen from —CN, —CF₃, or —COOR₆₈; or R_(67′) being        —C(O)V″, wherein V″ being chosen from hydrogen, C₁–C₆ alkoxy,        phenoxy, mono- or di-(C₁–C₆)alkyl substituted phenoxy, mono- or        di-(C₁–C₆)alkoxy substituted phenoxy, an unsubstituted, mono- or        di-substituted aryl group, phenyl or naphthyl, amino,        mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, phenylamino, mono-        or di-(C₁–C₆)alkyl substituted phenylamino, or mono- or        di-(C₁–C₆)alkoxy substituted phenylamino; each of said aryl        group substituents being independently chosen from C₁–C₆ alkyl        or C₁–C₆ alkoxy;    -   (v)-CH(Q′″)₂, Q′″ being chosen from —-CN or —COOR₆₉ and R₆₉        being chosen from hydrogen, C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl,        mono(C₁–C₆)alkyl substituted phenyl (C₁–C₃)alkyl,        mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl or an        unsubstituted, mono- or di-substituted aryl group, phenyl or        naphthyl; each of said aryl group substituents being        independently chosen from C₁–C₆ alkyl or C₁–C₆ alkoxy;    -   (vi) —CH(R₇₀)G″, R₇₀ being chosen from hydrogen, C₁–C₆ alkyl or        an unsubstituted, mono- or di-substituted aryl group, phenyl or        naphthyl, and G″ being chosen from —COOR₆₉, —COR₇₁ or —CH₂OR₇₂,        wherein R₇₁ being chosen from hydrogen, C₁–C₆ alkyl, an        unsubstituted, mono- or di-substituted aryl group, phenyl or        naphthyl, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino,        phenylamino, mono- or di-(C₁–C₆)alkyl substituted phenylamino,        mono- or di-(C₁–C₆)alkoxy substituted phenylamino,        diphenylamino, mono- or di(C₁–C₆)alkyl substituted        diphenylamino, mono- or di(C₁–C₆)alkoxy substituted        diphenylamino, morpholino or piperidino; R₇₂ being chosen from        hydrogen, —C(O)R₆₉, C₁–C₆ alkyl, C₁–C₃ alkoxy(C₁–C₆)alkyl,        phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted        phenyl(C₁–C₃)alkyl or an unsubstituted, mono- or di-substituted        aryl group, phenyl or naphthyl, each of said aryl group        substituents being independently chosen from C₁–C₆ alkyl or        C₁–C₆ alkoxy;    -   (vii) the group T being the same as described hereinbefore        in (d) (i) for the material represented by graphic formula II;        or    -   (viii) R₆₂ and R₆₃ together form an oxo group or a substituted        or unsubstituted spiro-carbocyclic ring containing 3 to 6 carbon        atoms or a substituted or unsubstituted spiro-heterocyclic group        containing 1 or 2 oxygen atoms and 3 to 6 carbon atoms including        the spirocarbon atom, said spiro-carbocyclic ring and        spiro-heterocyclic group being annellated with 0, 1 or 2 benzene        rings, said substituents being hydrogen or C₁–C₆ alkyl;

(d) R₆₄ is chosen from hydrogen, C₁–C₆ alkyl or the group R_(a) chosenfrom:

-   -   (i) —OR₇₃, R₇₃ being chosen from phenyl(C₁–C₃)alkyl, C₁–C₆        alkyl, mono(C₁–C₆)alkyl substituted phenyl(C₁–C₃)alkyl,        mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl, C₁–C₆        alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl, mono(C₁–C₄)alkyl        substituted C₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆        fluoroalkyl, allyl or —CH(R₆₈)Q″ described in (c) (i); or    -   (ii) an amino group described hereinbefore in (b) (i), (ii),        (iii), (iv) or (v) for the material represented by graphic        formula IV;

(e) R₆₅ is chosen from hydrogen, C₁–C₆ alkyl or R_(a), said R_(a) beingthe same as described hereinbefore in (d);

(f) R₆₆ is chosen from hydrogen, C₁–C₆ alkyl or R_(a), said R_(a) beingthe same as described hereinbefore in (d); or

(g) R₆₅ and R₆₆ together form one of the following graphic formulae:

wherein J′ and K′ being independently chosen for each occurrence in eachformula from oxygen or —N(R₁₅)—, said groups R₁₅ R₁₈ and R₁₉ each beingthe same as described hereinbefore in (b) and (d) (vi) for the materialrepresented by graphic formula II;

(h) B and B′ are each independently chosen from the groups describedhereinbefore in Cd) for the material represented by graphic formula II.

In another non-limiting embodiment, the indenonaphthopyran isrepresented by graphic formula XIII wherein:

(a) R₆₁ is represented by:

-   -   (i) —SR₆₇, R₆₇ being C₁–C₆ alkyl or aryl;    -   (ii) an amino group described hereinbefore in (b) (i), (ii)        or (iii) for the material represented by graphic formula IV;

(b) R₆₁′ is independently chosen for each occurrence from C₁–C₆ alkyl orC₁–C₆ alkoxy and q being the integer 1;

(c) R₆₂ and R₆₃ are each independently chosen from:

-   -   (i) hydrogen, hydroxy, C₁–C₁₂ alkyl, C₃–C₁₂ alkylidene, C₃–C₇        cycloalkyl, or —C(O)W″, wherein W″ being the same group        described hereinbefore in (b) for the material represented by        graphic formula XIA or XIB;    -   (ii) an unsubstituted, mono- di- or tri-substituted group chosen        from phenyl; each of said phenyl substituents in (c) (ii) being        chosen independently for each occurrence from chloro, fluoro,        C₁–C₆ alkyl or C₁–C₆ alkoxy;    -   (iii) a monosubstituted phenyl, said phenyl having a substituent        located at the para position being as described hereinbefore        in (d) for the material represented by graphic formula II;    -   (iv) OR_(67′)R₆₇, being chosen from C₁–C₆ alkyl,        phenyl(C₁–C₃)alkyl, C₁–C₆ alkoxy(C₂–C₄)alkyl or        tri(C₁–C₆)alkylsilyl;    -   (v) —CH(Q′″)₂, Q′″ being chosen from —COOR₆₉ and R₆₉ being C₁–C₆        alkyl;    -   (vi) —CH(R₇₀)G″, R₇₀ being chosen from hydrogen, C₁–C₆ alkyl or        an unsubstituted, mono- or di-substituted aryl group, phenyl or        naphthyl, and G″ being chosen from —COOR₆₉, —COR₇₁ or —CH₂OR₇₂,        wherein R₇₁ being chosen from hydrogen, C₁–C₆ alkyl, an        unsubstituted, mono- or di-substituted aryl group, phenyl or        naphthyl, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino,        phenylamino, mono- or di-(C₁–C₆)alkyl substituted phenylamino,        mono- or di-(C₁–C₆)alkoxy substituted phenylamino,        diphenylamino, mono- or di(C₁–C₆)alkyl substituted        diphenylamino, mono- or di(C₁–C₆)alkoxy substituted        diphenylamino, morpholino or piperidino; R₇₂ being chosen from        hydrogen, —C(O)R₆₉, C₁–C₆ alkyl, C₁–C₃ alkoxy(C₁–C₆)alkyl,        phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted        phenyl(C₁–C₃)alkyl or an unsubstituted, mono- or di-substituted        aryl group, phenyl or naphthyl, each of said aryl group        substituents being independently chosen from C₁–C₆ alkyl or        alkoxy;    -   (vii) the group T described hereinbefore in (d) (i) for the        material represented by graphic formula II; or    -   (viii) R₆₂ and R₆₃ together form an oxo group or a substituted        or unsubstituted spiro-carbocyclic ring containing 3 to 6 carbon        atoms or a substituted or unsubstituted spiro-heterocyclic group        containing 1 or 2 oxygen atoms and 3 to 6 carbon atoms including        the spirocarbon atom, said spiro-carbocyclic ring and        spiro-heterocyclic group being annellated with 0, 1 or 2 benzene        rings, said substituents being hydrogen or C₁–C₆ alkyl;

(d) R₆₄ is chosen from hydrogen, C₁–C₆ alkyl or the group R_(a) chosenfrom:

-   -   (i) —OR₇₃, R₇₃ being chosen from phenyl(C₁–C₃)alkyl, C₁–C₆        alkyl, mono(C₁–C₆)alkyl substituted phenyl(C₁–C₃)alkyl,        mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl, C₁–C₆        alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl, mono(C₁–C₄)alkyl        substituted C₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆        fluoroalkyl, allyl or —CH(R₆₈)Q″; or    -   (ii) an amino group described hereinbefore in (b) (i), (ii)        or (iii) for the material represented by graphic formula IV;

(e) R₆₅ is chosen from hydrogen, C₁–C₆ alkyl or R_(a), said R_(a) beingthe same as described hereinbefore in (d);

(f) R₆₆ is chosen from hydrogen, C₁–C₆ alkyl or R_(a), said R_(a) beingthe same as described hereinbefore in (d); or

(g) R₆₅ and R₆₆ together form one of the following graphic formulae:

wherein J′ and K′ being independently chosen for each occurrence in eachformula from oxygen or —N(R₁₅)—, said groups R₁₅, R₁₉ and R₂₀ each beingthe same as described hereinbefore in (b) and (d) (vi) for the materialrepresented by graphic formula II;

(h) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the indenonaphthopyran representedby graphic formula XIII is chosen from:

-   (a)    3,3-di(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;-   (b)    3-phenyl-3-(4-morpholino-phenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;-   (c) 3,3-di(4-(2-methoxyethoxyphenyl)    )-11-morpholino-13,13-dimethyl-3H,    13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;-   (d)    3,3-di(4-methoxyphenyl)-11-morpholino-13-hydroxy-13-ethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;-   (e)    3,3-di(4-methoxyphenyl)-10-methoxy-11-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;-   (f)    3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-10-methoxy-11-morpholino-13,13-dimethyl-3H,    13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;-   (g)    3-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;-   (h)    3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-3H,    13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;-   (i)    3,3-di(2-methoxyethoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;    or-   (j) mixtures thereof.

The materials represented by graphic formula XIII can be produced by themethods disclosed in U.S. patent application Ser. No. 10/393,177 filedeven herewith on Mar. 20, 2003, which disclosure is incorporated hereinby reference.

In one non-limiting embodiment, a photochromic material is chosen from aindenonaphthopyran represented by the following graphic formula XIV:

wherein,

(a) R₇₄ and R₇₅ are each the same as R₆₂ and R₆₃ groups describedhereinbefore in (c) for the material represented by graphic formulaXIII;

(b) each R₇₆ is independently chosen for each occurrence fromdi(C₁–C₆)alkylamino, dicyclohexylamino, diphenylamino, piperidyl,morpholinyl, pyridyl, a group T, described hereinbefore in (d) (i) forthe material represented by graphic formula II, and group —C(O)W″described hereinbefore in (b) for the material represented by graphicformula XIII, and q is the integer 0, 1, or 2; or when q is 2, and theR₇₆ substituents are adjacent, each pair of substituents independentlyforms a substituted or unsubstituted fused carbocyclic or heterocyclicring chosen from benzo, pyridino, pyrazino, pyrimidino, furano,dihydrofurano, 1,3-dioxolo, 1,4-dioxolo, 1,3-dioxino, 1,4-dioxino,thiopheno, benzofuro, benzothieno, indolo, or indeno, the substituentsof said fused carbocyclic or heterocyclic ring being chosen fromhalogen, C₁–C₆ alkyl, C₁–C₆ alkoxy, amino, mono- or di-substitutedamino, said amino substituents being chosen from C₁–C₆ alkyl, phenyl,benzyl or naphthyl; said first R₇₆ ring being fused to the o, p or qside and said second R₇₆ ring being fused to the g, h, or i side of theindenonaphthopyran;

(c) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In another non-limiting embodiment, the indenonaphthopyran isrepresented by graphic formula XIV wherein:

(a) R₇₄ and R₇₅ are each the same as R₆₂ and R₆₃ groups describedhereinbefore in (c) for the material represented by graphic formulaXIII;

(b) each R₇₆ is independently chosen from di(C₁–C₆)alkylamino,dicyclohexylamino, diphenylamino, piperidyl, morpholinyl, pyridyl,halogen, or group —C(O)W″ described hereinbefore in (d) for the materialrepresented by graphic formula XIII, and q is the integer 0, 1, or 2; orwhen q is 2, and the R₇₆ substituents are adjacent, each pair ofsubstituents independently forms a substituted or unsubstituted fusedcarbocyclic or heterocyclic ring chosen from benzo, dihydrofurano,1,4-dioxolo, 1,3-dioxino, or benzofuro, the substituents of said fusedcarbocyclic or heterocyclic ring being chosen from the group consistingof C₁–C₆ alkyl or C₁–C₆ alkoxy;

(c) B and B′ are each independently chosen from the groups describedhereinbefore in (d) for the material represented by graphic formula II.

In a further non-limiting embodiment, the indenonaphthopyran representedby graphic formula XIV is chosen from:

-   (a)    3,3,9-triphenyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (b)    3,3-di(4-methoxyphenyl)-9-phenyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (c)    3-(4-methoxyphenyl)-3,9-diphenyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (d)    3-(4-morpholinophenyl)-3,9-diphenyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (e)    3-(4-methoxyphenyl)-3-phenyl-9-methyl-13-methoxy-9-(3-methoxyphenyl)-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (f)    3,3-di(4-methoxyphenyl)-9-methyl-13-methoxy-9-(3-methoxyphenyl)-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (g)    3,3-di(4-methoxyphenyl)-9-methyl-11-methoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho    [1,2-b]pyran;-   (h)    3,3-di(4-methoxyphenyl)-9,9-dimethyl-11-methoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (i)    3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-11-methoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (j)    3,3-di(4-methoxyphenyl)-9,9-dimethyl-7,11-dimethoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (k)    3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-7,11-dimethoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (l)    3-(4-morpholinophenyl)-3-phenyl-9,9-dimethyl-7,11-dimethoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (m)    3,3-di(4-methoxyphenyl)-9-methyl-11,13-dimethoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (n)    3-(4-methoxyphenyl)-3-phenyl-9-methyl-11,13-dimethoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (o)    3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;-   (p)    3,3-di(4-methoxyphenyl-9,9-dimethyl-11-fluoro-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;    or-   (q) mixtures thereof.

The materials represented by graphic formula XIV can be produced by themethods disclosed in U.S. patent application Ser. No. 10/039,984 filedon Oct. 29, 2001, which disclosure is incorporated herein by reference.

BWS photochromic materials, including those represented by graphicformulae XIII or a mixture thereof can be used in various non-limitingapplications in which photochromic materials can be employed, such asoptical lenses, e.g., vision correcting ophthalmic lenses and planolenses, face shields, goggles, visors, camera lenses, windows,automotive windshields, aircraft and automotive transparencies, e.g.,T-roofs, sidelights and backlights, polymeric coatings, plastic filmsand sheets, textiles and pigmented liquids or pastes, e.g., paints andinks used as verification marks on security documents, e.g., documentssuch as banknotes, passports and drivers' licenses for whichauthentication or verification of authenticity may be desired.

In one non-limiting embodiment, it is contemplated that the BWSphotochromic materials of the present invention can each be used aloneor in combination with other BWS photochromic materials of the presentinvention, or in combination with one or more other photochromicmaterials, e.g., photochromic materials having at least one activatedabsorption maxima within the range of between about 400 and 700nanometers, and can be incorporated, e.g., dissolved or dispersed, in apolymeric organic host material used to prepare photochromic articles,which become colored when activated to an appropriate hue.

In one non-limiting embodiment, the other photochromic materials caninclude the following classes of materials: chromenes, e.g.,naphthopyrans, benzopyrans, indenonaphthopyrans and phenanthropyrans;spiropyrans, e.g., spiro(benzindoline)naphthopyrans,spiro(indoline)benzopyrans, spiro(indoline)naphthopyrans,spiro(indoline)quinopyrans and spiro(indoline)pyrans; oxazines, e.g.,spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines,spiro(benzindoline)pyridobenzoxazines, spiro(benzindoline)naphthoxazinesand spiro(indoline)benzoxazines; mercury dithizonates, fulgides,fulgimides and mixtures of such photochromic materials.

Such photochromic materials and complementary photochromic materials aredescribed in U.S. Pat. No. 4,931,220 at column 8, line 52 to column 22,line 40; U.S. Pat. No. 5,645,767 at column 1, line 10 to column 12, line57; U.S. Pat. No. 5,658,501 at column 1, line 64 to column 13, line 17;U.S. Pat. No. 6,153,126 at column 2, line 18 to column 8, line 60; U.S.Pat. No. 6,296,785 at column 2, line 47 to column 31, line 5; U.S. Pat.No. 6,348,604 at column 3, line 26 to column 17, line 15; and U.S. Pat.No. 6,353,102 at column 1, line 62 to column 11, line 64, thedisclosures of the aforementioned patents are incorporated herein byreference. Spiro(indoline)pyrans are also described in the text,Techniques in Chemistry, Volume III, “Photochromism”, Chapter 3, GlennH. Brown, Editor, John Wiley and Sons, Inc., New York, 1971.

In another non-limiting embodiment, polymerizable photochromicmaterials, such as polymerizable naphthoxazines disclosed in U.S. Pat.No. 5,166,345 at column 3, line 36 to column 14, line 3; polymerizablespirobenzopyrans disclosed in U.S. Pat. No. 5,236,958 at column 1, line45 to column 6, line 65; polymerizable spirobenzopyrans andspirobenzothiopyrans disclosed in U.S. Pat. No. 5,252,742 at column 1,line 45 to column 6, line 65; polymerizable fulgides disclosed in U.S.Pat. No. 5,359,085 at column 5, line 25 to column 19, line 55;polymerizable naphthacenediones disclosed in U.S. Pat. No. 5,488,119 atcolumn 1, line 29 to column 7, line 65; polymerizable spirooxazinesdisclosed in U.S. Pat. No. 5,821,287 at column 3, line 5 to column 11,line 39; polymerizable polyalkoxylated naphthopyrans disclosed in U.S.Pat. No. 6,113,814 at column 2, line 23 to column 23, line 29; and thepolymerizable photochromic compounds disclosed in WO97/05213 andapplication Ser. No. 09/828,260 filed Apr. 6, 2001 can be used. Thedisclosures of the aforementioned patents on polymerizable photochromicmaterials are incorporated herein by reference.

Other non-limiting embodiments of photochromic materials that can beused include organo-metal dithiozonates, e.g., (arylazo)-thioformicarylhydrazidates, e.g., mercury dithizonates which are described in, forexample, U.S. Pat. No. 3,361,706 at column 2, line 27 to column 8, line43; and fulgides and fulgimides, e.g., the 3-furyl and 3-thienylfulgides and fulgimides, which are described in U.S. Pat. No. 4,931,220at column 1, line 39 through column 22, line 41, the disclosures ofwhich are incorporated herein by reference.

An additional non-limiting embodiment is a form of organic photochromicmaterial resistant to the effects of a polymerization initiator that canalso be used in the photochromic articles of the present invention. Suchorganic photochromic materials include photochromic compoundsencapsulated in metal oxides, the latter of which are described in U.S.Pat. Nos. 4,166,043 and 4,367,170 at column 1 line 36 to column 7, line12, which disclosure is incorporated herein by reference.

In another non-limiting embodiment, inorganic photochromic systemscontemplated for use with the BWS materials of the present inventiontypically contain crystallites of silver halide, cadmium halide and/orcopper halide. Other non-limiting inorganic photochromic glass systemscan be prepared by the addition of europium (II) and/or cerium (III) toa soda-silica glass. Such inorganic photochromic glass systems aredescribed in Kirk Othmer Encyclopedia of Chemical Technology, 4thEdition, Volume 6, pages 322–325, which disclosure is incorporatedherein by reference.

The photochromic materials described herein, e.g., the BWS materials ofthe present invention and other photochromic materials, can be chosenfrom a variety of materials. Non-limiting examples include: of course, asingle photochromic compound; a mixture of photochromic compounds; amaterial comprising at least one photochromic compound, such as aplastic polymeric resin or an organic monomeric or oligomeric solution;a material such as a monomer or polymer to which at least onephotochromic compound is chemically bonded; a material comprising and/orhaving chemically bonded to it at least one photochromic compound, theouter surface of the material being encapsulated (encapsulation is aform of coating), for example with a polymeric resin or a protectivecoating such as a metal oxide that prevents contact of the photochromicmaterial with external materials such as oxygen, moisture and/orchemicals that have a negative effect on the photochromic material, suchmaterials can be formed into a particulate prior to applying theprotective coating as described in U.S. Pat. Nos. 4,166,043 and4,367,170; a photochromic polymer, e.g., a photochromic polymercomprising photochromic compounds bonded together; or mixtures thereof.

The organic photochromic materials and BWS materials of the presentinvention to be used in a photochromic article can be associated with apolymeric organic host material or other substrate by various means. Ina series of non-limiting embodiments, they can be incorporated, e.g.,dissolved and/or dispersed, into the host material, polymerized withother components of the host material, e.g., in a reaction injectionmolding, and/or incorporated into an at least partial coating or filmapplied to a substrate, e.g., an at least partially cured polymericcoating or a film applied to one surface of the substrate.

In one non-limiting embodiment, a photochromic article adapted to retainat least 12 percent of the delta OD measured in the Outdoor Test whentested in the Behind the Windshield Test can be prepared by a methodcomprising:

a) obtaining a substrate;

b) obtaining a photochromic material adapted to change from anunactivated form to an activated form by exposure to radiationsubstantially in the wavelength range from 380 to 410 nanometers whenmeasured over a range of from 380 to 700 nanometers;

c) introducing the photochromic material together with said substrate bya method chosen from:

-   -   i) introducing photochromic material (b) with the starting        materials used to form said substrate;    -   ii) at least partially imbibing photochromic material (b) into        at least one surface of said substrate;    -   iii) applying at least a partial coating of a polymeric coating        composition comprising photochromic material (b) to at least one        surface of said substrate;    -   iv) at least partially connecting a superstrate comprising        photochromic material (b) to at least one surface of said        substrate; or    -   v) combinations of i), ii), ii) or iv).

In another non-limiting embodiment, the aforementioned method furthercomprises adding a photochromic material (c) that is different fromphotochromic material (b), in (c) (i), (ii), (iii), (iv) or (v). In afurther non-limiting embodiment, the aforementioned method furthercomprises adding a fixed tint dye in (c) (i), (ii), (iii), (iv) or (v).

An alternate non-limiting embodiment for producing a photochromicarticle adapted to exhibit an unactivated state luminous transmittanceof greater than 70 percent at 23° C., an activated state luminoustransmittance at saturation less than 30 percent when activated at 23°C. by simulated sunlight from a xenon arc lamp set at 6.7 Watts/meter²UVA and 50,000 lumens/meter², and an activated state luminoustransmittance at saturation less than 60 percent when activated at 28°C. by simulated sunlight from a xenon arc lamp through an UV blockingtransparency rendering an irradiance integrated between 380 and 420nanometers of 0.75 Watts/meter² and 1,700 lumens/meter²; said methodcomprising:

a) obtaining a substrate;

b) obtaining a photochromic material adapted to change from anunactivated form to an activated form by exposure to radiationsubstantially in the wavelength range from 380 to 410 nanometers whenmeasured over a range of from 380 to 700 nanometers;

c) introducing the photochromic material with said substrate by a methodchosen from:

-   -   i) introducing photochromic material (b) with the starting        materials used to form the substrate;    -   ii) at least partially imbibing photochromic material (b) into        at least one surface of the substrate;    -   iii) applying at least a partial coating of a polymeric coating        composition comprising photochromic material (b) to at least one        surface of the substrate;    -   iv) at least partially connecting a superstrate comprising        photochromic material (b) to at least one surface of the        substrate; or    -   v) a combination of i), ii), ii) or iv).

In another non-limiting embodiment, the aforementioned method furthercomprises adding a photochromic material (c) that is different fromphotochromic material (b), in (c) (i), (ii), (iii), (iv) or (v). In afurther non-limiting embodiment, the aforementioned method furthercomprises adding a fixed tint dye in (c) (i), (ii), (iii), (iv) or (v).

The photochromic articles prepared by the aforementioned methods can besubstantially free of ultraviolet radiation absorbing materials adaptedto substantially inhibit the activation of the photochromic material byradiation below 380 nm.

Potential substrates for the application of coatings containing BWSphotochromic materials or a mixture of BWS photochromic materials andother photochromic include any type of material. Non-limiting examplesinclude, paper, glass, ceramics, wood, masonry, textiles, metals andpolymeric organic host materials.

Each of the BWS photochromic materials with or without the otherphotochromic materials described herein can be used in amounts (or in aratio) such that a host material or substrate to which the BWSphotochromic materials or mixture of BWS photochromic materials andother photochromics is associated, exhibits a desired resultant color,e.g., a substantially neutral color when activated with unfilteredsunlight, e.g., as near a neutral color as possible given the colors ofthe activated photochromic materials, and a retained coloration,measured as delta OD or ΔOD, of at least 12 percent of that demonstratedunder conditions of outdoor exposure when tested in the Behind theWindshield Test described herein in Example 13. In an alternatenon-limiting embodiment, the photochromic articles of the presentinvention demonstrate an activated state luminous transmittance atsaturation less than 60 percent when activated under the conditions inthe Behind the Windshield Test. In one non-limiting embodiment, the BWSphotochromic materials could be used to produce articles having a widerange of colors, e.g., pink. Further discussion of neutral colors andways to describe colors can be found in U.S. Pat. No. 5,645,767 column12, line 66 to column 13, line 19.

In one non-limiting embodiment, the amount of the BWS photochromicmaterials to be applied to or incorporated into a polymeric coatingcomposition and/or polymeric host material of the photochromic articleof the present invention can vary widely. Typically, a sufficient amountis used to produce the desired retained coloration behind an UV blockingtransparency such as a vehicular windshield. Generally such an amountcan be described as a behind the UV blocking transparency activatingamount or behind the windshield activating amount. The particular amountused depends often upon the retained coloration desired upon irradiationthereof and upon the method used to incorporate or apply the BWSphotochromic materials. Typically, in one non-limiting embodiment, themore BWS photochromic material applied or incorporated, the greater isthe coloration retained behind the windshield up to a certain limit.There is a point after which the addition of any more material will nothave a noticeable effect, although more material can be added, ifdesired

In one non-limiting embodiment, the amount of the other photochromicmaterials to be incorporated into a polymeric coating composition and/orpolymeric host material can vary widely. Typically, a sufficient amountis used to produce a photochromic effect discernible to the naked eyeupon activation. Generally such amount can be described as aphotochromic amount. The particular amount used depends often upon theintensity of color desired upon irradiation thereof and upon the methodused to incorporate the photochromic materials. Typically, in onenon-limiting embodiment, the more photochromic incorporated, the greateris the color intensity up to a certain limit. There is a point afterwhich the addition of any more material will not have a noticeableeffect, although more material can be added, if desired.

The relative amounts of the aforesaid BWS photochromic materials orcombinations of BWS photochromic materials and other photochromicmaterials used will vary and depend in part upon the relativeintensities of the color of the activated species of such materials, theultimate color desired, the retained coloration desired and the methodof application to the host material and/or substrate. In onenon-limiting embodiment, the amount of total photochromic material whichincludes BWS photochromic materials, other photochromic materials orboth, incorporated by imbibition into a photochromic optical hostmaterial can vary widely. In alternate non-limiting embodiments, it canrange from about 0.01 to about 2.0, or from 0.05 to about 1.0,milligrams per square centimeter of surface to which the photochromicmaterial is incorporated or applied. The amount of total photochromicmaterial incorporated or applied to the host material can range betweenany combination of these values, inclusive of the recited range, e.g.,0.015 to 1.999 milligrams per square centimeter.

In another non-limiting embodiment, the total amount of photochromicmaterial incorporated into a polymerizable composition for forming acoating, film or polymerizate can vary widely, e.g., it can range from0.01 to 40 weight percent based on the weight of the solids in thepolymerizable composition. In alternate non-limiting embodiments, theconcentration of photochromic materials ranges from 0.1 to 30 weightpercent, from 1 to 20 weight percent, from 5 to 15 weight percent, orfrom 7 to 14 weight percent. The amount of photochromic material in thecoating can range between any combination of these values, inclusive ofthe recited range, e.g., 0.011 to 39.99 weight percent.

In one non-limiting embodiment, compatible (chemically and color-wise)tints, e.g., dyes, can be added or applied to the host material used toproduce the photochromic article to achieve a more aesthetic result, formedical reasons, or for reasons of fashion. The particular dye selectedwill vary and depend on the aforesaid need and result to be achieved. Inone non-limiting embodiment, the dye can be selected to complement thecolor resulting from the activated photochromic materials, e.g., toachieve a more neutral color or absorb a particular wavelength ofincident light. In another non-limiting embodiment, the dye can beselected to provide a desired hue to the host material when thephotochromic materials are in an unactivated state.

In various non-limiting embodiments, adjuvant materials can also beincorporated into host material used to produce the photochromicarticle. Such adjuvants can be used, prior to, simultaneously with orsubsequent to application or incorporation of the photochromic material.For example, ultraviolet light absorbers can be admixed withphotochromic materials before their addition to the composition or suchabsorbers can be superposed, e.g., superimposed, as a coating betweenthe photochromic article and the incident light.

Further, stabilizers can be admixed with the photochromic materialsprior to their addition to the composition to improve the light fatigueresistance of the photochromic materials provided that such stabilizersdo not prevent the photochromic materials from activating. Non-limitingexamples of stabilizers include hindered amine light stabilizers (HALS),asymmetric diaryloxalamide (oxanilide) compounds and singlet oxygenquenchers, e.g., a nickel ion complex with an organic ligand,polyphenolic antioxidants or mixtures of such stabilizers arecontemplated. In one non-limiting embodiment, they can be used alone orin combination. Such stabilizers are described in U.S. Pat. Nos.4,720,356, 5,391,327 and 5,770,115.

The BWS photochromic materials, other photochromic materials orcombinations thereof can be associated with the host material by variousmethods described in the art. In various non-limiting embodiments, thetotal amount of photochromic material can be incorporated into the hostmaterial used to form the photochromic article by various methods suchas by adding the photochromic materials to one or more of the materialsused to form the host material. In one non-limiting embodiment when thehost material is a polymeric coating or film, the photochromic materialscan be dissolved and/or dispersed in an aqueous or organic solvent priorto being incorporated into one or more of the components of the coatingor film composition used to form the coating Alternatively, thephotochromic materials can be incorporated into the at least partiallycured coating or film by imbibition, permeation or other transfermethods as known by those skilled in the art.

When at least partially cured polymers or polymerizates are used as thehost material for the photochromic materials, various non-limitingembodiments include preparation of a photochromic article by injecting apolymerizable composition with photochromic materials into a mold andpolymerizing it by what, for example, is commonly referred to in the artas a cast-in-place process. Polymerizates, e.g., lenses, prepared bycast polymerization in the absence of a photochromic amount of aphotochromic material can be used to prepare photochromic articles byapplying or incorporating photochromic materials into the polymerizateby art-recognized methods.

Such non-limiting art-recognized methods include: (a) dissolving ordispersing the photochromic materials within the polymerizate, e.g.,imbibition of the photochromic materials into the polymerizate byimmersion of the polymerizate in a hot solution of the photochromicmaterials or by thermal transfer; (b) providing the photochromicmaterial as a separate layer between adjacent layers of thepolymerizate, e.g., as a part of a polymer film; and (c) applying thephotochromic material as part of a coating or film placed or laminatedon the surface of the polymerizate. The term “imbibition” or “imbibe” isintended to mean and include permeation of the photochromic materialsindividually or with other non-photochromic materials into thepolymerizate, solvent assisted transfer absorption of the photochromicmaterials into a polymerizate, vapor phase transfer, and other suchtransfer mechanisms.

In the context of the present invention, the nature of the polymericsubstrate, polymeric film or polymeric coating, collectively referred toas the polymeric host, can vary widely. Generally the polymeric host issuch that it allows the BWS materials of the present invention and otherphotochromic materials to reversibly transform between their “open” and“closed” forms. In one non-limiting embodiment, the polymer and/orpolymeric coating composition used to produce the photochromic articlesof the present invention comprises compositions adapted to providethermoplastic or thermosetting organic polymeric materials that aredescribed in the Kirk-Othmer Encyclopedia of Chemical Technology, FourthEdition, Volume 6, pages 669 to 760, which disclosure is incorporatedherein by reference. Such polymeric host materials can be transparent,translucent or opaque; but desirably are transparent. In anothernon-limiting contemplated embodiment is a polymeric material that uponcuring forms an at least partially cured polymeric coating chosen frompolyurethanes, aminoplast resins, poly(meth)acrylates, e.g.,polyacrylates and polymethacrylates, polyanhydrides, polyacrylamides,epoxy resins and polysilanes.

The various coating compositions described below are well known and aremade with components and according to methods well understood andappreciated to those skilled in the art. Suitable substrates for theapplication of coatings containing the BWS materials or a mixture of theBWS materials and other photochromic materials include any type ofsubstrate. Non-limiting examples include, paper, glass, ceramics, wood,masonry, textiles, metals and polymeric organic host materials.

The photochromic polyurethane coatings that can be used to prepare thephotochromic coated articles of the present invention, in onenon-limiting embodiment, can be produced by the catalyzed or uncatalyzedreaction of an organic polyol component and an isocyanate component inthe presence of photochromic compound(s). Materials and methods for thepreparation of polyurethanes are described in Ullmann's Encyclopedia ofIndustrial Chemistry, Fifth Edition, 1992, Vol. A21, pages 665 to 716.Non-limiting examples of methods and materials, e.g., organic polyols,isocyanates and other components, which can be used to prepare thepolyurethane coating are disclosed in U.S. Pat. Nos. 4,889,413 and6,187,444B1.

The photochromic aminoplast resin coating composition that can be usedto produce the photochromic coated articles of the present invention, inone non-limiting embodiment, can be prepared by combining a photochromicmaterial with the reaction product of a functional component(s) havingat least two functional groups chosen from hydroxyl, carbamate, urea ora mixture thereof and an aminoplast resin, e.g., crosslinking agent asdescribed in U.S. Pat. Nos. 4,756,973, 6,432,544B1 and 6,506,488.

Photochromic polysilane coating compositions contemplated for use inpreparing the photochromic coated articles of the present invention, inone non-limiting embodiment, are prepared by hydrolyzing at least onesilane monomer such as glycidoxypropyltrimethoxysilane,vinyltrimethoxysilane, methacryloxypropyltrimethoxysilane,tetramethoxysilane, tetraethoxysilane and/or methyltrimethoxysilane andcombining the hydrolyzate with at least one photochromic material asdescribed in U.S. Pat. No. 4,556,605.

Photochromic poly(meth)acrylate coating compositions contemplated foruse in preparing the photochromic coated articles of the presentinvention can be prepared, in one non-limiting embodiment, by combiningphotochromic compound(s) with mono-, di- or multi-functional(meth)acrylates as described in U.S. Pat. Nos. 6,025,026 and 6,150,430and WO publication 01/02449 A2.

The polyanhydride photochromic coating composition that can be used toprepare the photochromic coated articles of the present invention can beprepared in one non-limiting embodiment, by the reaction of ahydroxyl-functional component and a polymeric anhydride-functionalcomponent in a composition including at least one organic photochromicmaterial as described in U.S. Pat. No. 6,432,544B1. Non-limitingexamples of hydroxyl-functional components, anhydride-functionalcomponent(s) and other components that can be used to prepare thepolyanhydride photochromic coatings are disclosed in U.S. Pat. Nos.4,798,745, 4,798,746 and 5,239,012.

Photochromic polyacrylamide coating compositions contemplated for use inpreparing the photochromic coated articles of the present invention, inone non-limiting embodiment, can be prepared by combining a photochromiccomponent with the free radical initiated reaction product of apolymerizable ethylenically unsaturated composition comprisingN-alkoxymethyl(meth)acrylamide and at least one other copolymerizableethylenically unsaturated monomer as described in U.S. Pat. No.6,060,001. Methods for preparing N-alkoxymethyl(meth)acrylamidefunctional polymer are described in U.S. Pat. No. 5,618,586.

The photochromic epoxy resin coating compositions that can be used toprepare the photochromic coated articles of the present invention, inone non-limiting embodiment, can be prepared by combining photochromiccompound(s), epoxy resins or polyepoxides and curing agents as describedin U.S. Pat. Nos. 4,756,973 and 6,268,055B1.

In another non-limiting embodiment, the types of photochromic polymericcoatings comprising the film-forming polymers and the BWS photochromicmaterials of the present invention with or without other photochromiccompounds include paints, e.g., a pigmented liquid or paste used for thedecoration, protection and/or the identification of a substrate; andinks, e.g., a pigmented liquid or paste used for writing and printing onsubstrates such as in producing verification marks on securitydocuments, e.g., documents such as banknotes, passport and drivers'licenses, for which authentication or verification of authenticity maybe desired.

Application of the polymeric coating can be by any of the methods usedin coating technology, non-limiting examples include, spray coating,spin coating, spin and spray coating, spread coating, curtain coating,dip coating, casting or roll-coating and methods used in preparingoverlays, such as the method of the type described in U.S. Pat. No.4,873,029. The application method selected also depends on the thicknessof the desired coating.

The thickness of the coatings on the photochromic articles of thepresent invention can vary widely. Coating having a thickness rangingfrom 1 to 50 microns can be applied by the methods used in coatingtechnology. Coating of a thickness greater than 50 microns can requirethe application of multiple coatings or molding methods typically usedfor overlays. In one non-limiting embodiment, the coating may range inthickness from 1 to 10,000 microns, e.g., from 5 to 1000, e.g., from 8to 400, e.g., from 10 to 250 microns. The thickness of the polymericcoating can range between any combination of these values, inclusive ofthe recited range, e.g., a thickness of from 20 to 200 microns.

Following application of the polymeric coating to the surface of thesubstrate, in one non-limiting embodiment, the coating is at leastpartially cured. In another non-limiting embodiment, the methods usedfor curing the photochromic polymeric coating include the methods usedfor forming an at least partially cured polymer. Such methods includeradical polymerization, thermal polymerization, photopolymerization or acombination thereof. Additional non-limiting methods include irradiatingthe coated substrate or at least partially cured polymer with infrared,ultraviolet, gamma or electron radiation so as to initiate thepolymerization reaction of the polymerizable components. This can befollowed by a heating step.

In one non-limiting embodiment, if required and if appropriate, thesurface of the substrate to be coated is cleaned prior to applying thephotochromic polymeric coating to produce the photochromic article ofthe present invention. This can be done for the purposes of cleaningand/or promoting adhesion of the coating. Effective treatment techniquesfor plastics and glass are known to those skilled in the art.

In some non-limiting embodiments, it may be necessary to apply a primerto the surface of the substrate before application of the photochromicpolymeric coating. The primer can serve as a barrier coating to preventinteraction of the coating ingredients with the substrate and viceversa, and/or as an adhesive layer to adhere the photochromic polymericcoating to the substrate. Application of the primer can be by any of themethods used in coating technology such as, for example, spray coating,spin coating, spin and spray coating, spread coating, dip coating,casting or roll-coating.

The use of protective coatings, some of which can containpolymer-forming organosilanes, as primers to improve adhesion ofsubsequently applied coatings has been described in U.S. Pat. No.6,150,430, which disclosure is incorporated herein by reference. In onenon-limiting embodiment, non-tintable coatings are used. Non-limitingexamples of commercial coating products include SILVUE® 124 and HI-GARD®coatings, available from SDC Coatings, Inc. and PPG Industries, Inc.,respectively. In addition, depending on the intended use of the coatedarticle, in one non-limiting embodiment, it can be necessary to apply anappropriate protective coating(s), such as an abrasion resistant coatingand/or coatings that can serve as oxygen barriers, onto the exposedsurface of the coating composition to prevent scratches from the effectsof friction and abrasion and interactions of oxygen with thephotochromic materials, respectively.

In some cases, the primer and protective coatings are interchangeable,e.g., the same coating can be used as the primer and the protectivecoating(s). Non-limiting examples of hardcoats include those based oninorganic materials such as silica, titania and/or zirconia as well asorganic hardcoats of the type that are ultraviolet light curable.

In one non-limiting embodiment, such protective coatings can be appliedto the surface of photochromic articles comprising at least partiallycured polymers containing photochromic materials.

In another non-limiting embodiment, the article of the present inventioncomprises a substrate to which a primer is applied followed by thephotochromic polymeric coating and a protective hardcoat. In a furthernon-limiting embodiment, the protective hardcoat is an organosilanehardcoat.

In additional non-limiting embodiments, other coatings or surfacetreatments, e.g., a tintable coating, antireflective surface, etc., canalso be, applied to the photochromic articles of the present invention.An antireflective coating, e.g., a monolayer or multilayer of metaloxides, metal fluorides, or other such materials, can be deposited ontothe photochromic articles, e.g., lenses, of the present inventionthrough vacuum evaporation, sputtering, or some other method.

In a further non-limiting embodiment, the photochromic articlecomprising an at least partially cured polymer and at least one BWSmaterial with or without other photochromic material further comprises asuperstrate, e.g., a film or sheet comprising at least one organicpolymeric material. The photochromic material can be located in thesuperstrate, the at least partially cured polymer or both. The organicpolymeric material of the superstrate is the same as the organicpolymeric material described hereinafter as the substrate or hostmaterial. Non-limiting examples of the organic polymeric materialsinclude thermosetting or thermoplastic materials, for example athermoplastic polyurethane superstrate.

In a still further non-limiting embodiment, the superstrate can beconnected to the polymer surface directly, but does not become thermallyfused to the substrate. In another non-limiting embodiment, thesuperstrate can be adheringly bonded to the substrate by becomingthermally fused with the subsurface of the substrate. General conditionsunder which superstrates are adheringly bonded to a substrate are knownto those skilled in the art. Non-limiting conditions for adheringlylaminating a superstrate to a substrate include heating to a temperatureof from 250–350° F. (121–177° C.) and applying pressure of from 150 to400 pounds per square inch (psi) (1034 to 2758 kPa). Sub-atmosphericpressures, e.g., a vacuum, can also be applied to draw down and conformthe superstrate to the shape of the substrate as known to those skilledin the art. Non-limiting examples include applying at a sub-atmosphericpressure within the range of from 0.001 mm Hg to 20 mm Hg (0.13 Pa to2.7 kPa).

After a laminate comprising a superstrate applied to as least onesurface of a substrate is formed, it can further comprise a protectivecoating or film superposed onto the superstrate. Such a protectivecoating or film, in one non-limiting embodiment, serves as an at leastpartially abrasion resistant coating or film. Non-limiting types ofprotective coatings include the aforedescribed hardcoats that arecurable by ultraviolet radiation and/or that contain organosilanes. Thethickness of the protective coating can vary widely and include theaforementioned range for the photochromic polymeric coatings.Non-limiting types of protective films include those made of organicpolymeric materials such as thermosetting and thermoplastic materials.In another non-limiting embodiment, the protective film is athermoplastic film made of polycarbonate. The thickness of theprotective film or sheet can vary widely. Typically, such films have athickness of from 1 to 20 mils (0.025 to 0.5 mm).

The host material for the BWS photochromic materials with or withoutother photochromic materials will usually be transparent, but may betranslucent or even opaque. The host material need only be pervious tothat portion of the electromagnetic spectrum, which activates thephotochromic material, e.g., that wavelength of ultraviolet (UV) lightthat produces the open or colored form of the photochromic and thatportion of the visible spectrum that includes the absorption maximumwavelength of the photochromic in its UV activated form, e.g., the openform. In one contemplated non-limiting embodiment, the host color shouldnot be such that it masks the color of the activated form of thephotochromic materials, e.g., so the change in color is readily apparentto the observer. Compatible tints may be applied to the host material asdescribed in U.S. Pat. No. 5,645,767 in column 13, line 59 to column 14,line 3.

In one contemplated non-limiting embodiment, the polymeric organic hostmaterial can be a solid transparent or optically clear material, e.g.,materials having a luminous transmittance of at least 70 percent and aresuitable for optical applications, such as optical elements chosen fromplano and ophthalmic lenses, ocular devices such as ophthalmic devicesthat physically reside in or on the eye, e.g., contact lenses andintraocular lenses, windows, automotive transparencies, e.g.,windshields, aircraft transparencies, plastic sheeting, polymeric films,etc.

Non-limiting examples of polymeric organic materials which can be usedas a host material for the BWS photochromic materials of the presentinvention with or without other photochromic materials or as a substratefor the photochromic polymeric coating include: poly(meth)acrylates,polyurethanes, polythiourethanes, thermoplastic polycarbonates,polyesters, poly(ethylene terephthalate), polystyrene, poly(alphamethylstyrene), copoly(styrene-methyl methacrylate),copoly(styrene-acrylonitrile), polyvinylbutyral, poly(vinyl acetate),cellulose acetate, cellulose propionate, cellulose butyrate, celluloseacetate butyrate, polystyrene or polymers, such as homopolymers andcopolymers prepared by polymerizing monomers chosen from bis(allylcarbonate) monomers, styrene monomers, diisopropenyl benzene monomers,vinylbenzene monomers, e.g., those described in U.S. Pat. No. 5,475,074,diallylidene pentaerythritol monomers, polyol (allyl carbonate)monomers, e.g., diethylene glycol bis(allyl carbonate), vinyl acetatemonomers, acrylonitrile monomers, mono- or polyfunctional, e.g., di- ormulti-functional, (meth)acrylate monomers such as (C₁–C₁₂)alkyl(meth)acrylates, e.g., methyl (meth)acrylate, ethyl (meth)acrylate,butyl (meth)acrylate etc., poly(oxyalkylene)(meth)acrylate,poly(alkoxylated phenol (meth)acrylates), diethylene glycol(meth)acrylates, ethoxylated bisphenol A (meth)acrylates, ethyleneglycol (meth)acrylates, poly(ethylene glycol) (meth)acrylates,ethoxylated phenol (meth)acrylates, alkoxylated polyhydric alcohol(meth)acrylates, e.g., ethoxylated trimethylol propane triacrylatemonomers, urethane (meth)acrylate monomers, such as those described inU.S. Pat. No. 5,373,033, or a mixture thereof. Further examples ofpolymeric organic host materials are disclosed in the U.S. Pat. No.5,753,146, column 8, line 62 to column 10, line 34.

In another non-limiting embodiment, transparent copolymers and blends oftransparent polymers are also suitable as polymeric materials. The hostmaterial can be an optically clear polymerized organic material preparedfrom a thermoplastic polycarbonate resin, such as the carbonate-linkedresin derived from bisphenol A and phosgene, which is sold under thetrademark, LEXAN; a polyester, such as the material sold under thetrademark, MYLAR; a poly(methyl methacrylate), such as the material soldunder the trademark, PLEXIGLAS; polymerizates of a polyol(allylcarbonate) monomer, especially diethylene glycol bis(allyl carbonate),which monomer is sold under the trademark CR-39, and polymerizates ofcopolymers of a polyol (allyl carbonate), e.g., diethylene glycolbis(allyl carbonate), with other copolymerizable monomeric materials,and copolymers with a polyurethane having terminal diacrylatefunctionality, as described in U.S. Pat. Nos. 4,360,653 and 4,994,208;and copolymers with aliphatic urethanes, the terminal portion of whichcontain allyl or acrylyl functional groups, as described in U.S. Pat.No. 5,200,483.

A further non-limiting embodiment is use of the BWS materials of thepresent invention and other photochromic materials with optical organicresin monomers used to produce optically clear coatings, films andpolymerizates, e.g., materials suitable for optical applications, suchas for example plano and ophthalmic lenses, windows, and automotivetransparencies. Examples of non-limiting embodiments includepolymerizates of optical resins sold by PPG Industries, Inc. as TRIVEXmonomers and under the CR-designation, e.g., CR-307, CR-407 and CR-607and the resins used to prepare hard or soft contact lenses. Methods forproducing both types of contact lenses are disclosed in U.S. Pat. No.5,166,345, column 11, line 52, to column 12, line 52.

Further non-limiting embodiments of optical resins include the resinsused to form soft contact lenses with high moisture content described inU.S. Pat. No. 5,965,630 and extended wear contact lenses described inU.S. Pat. No. 5,965,631.

The present invention is more particularly described in the followingexamples, which are intended as illustrative only, since numerousmodifications and variations therein will be apparent to those skilledin the art.

The following photochromic materials (PM) were used in the examplesdescribed hereinafter. PM-C, PM-D,PM-L, PM-M and PM-N represent BWSmaterials PM-A, PM-B, PM-E, PM-F, PM-G, PM-H, PM-I, PM-J, PM-K, PM-O,PM-P, and PM-AA and PM-BB represent other photochromic materials.

PM-A 7,7-diphenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran PM-B7-phenyl-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran PM-C3,3-di(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2- b]pyran PM-D3-(4-morpholinophenyl)-3-phenyl-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2- b]pyran PM-E7-(2-fluorophenyl)-7-(3-methyl-4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho [1,2-b]pyran PM-F3-(4-methoxyphenyl)-3-phenyl-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2- b]pyran PM-G2-(4-methoxyphenyl)-2-(2,4-dimethoxyphenyl)-7-diphenylmethyl-10-methyl-5-oxo-2H-5H-pyrano[3′,4′:3,4]naphtho[1,2-b]pyran PM-H7-(4-methoxyphenyl)-7-(2,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4] naphtho[1,2-b]pyran PM-I7-(4-morpholino-2-fluorophenyl)-7-(4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran PM-J7-(2-fluoro-4-methoxyphenyl)-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran PM-K7-(4-morpholino-2-fluorophenyl)-7-(3,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran PM-L3-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4] naphtho[1,2-b]pyranPM-M 3,3-di(2-methoxyethoxyphenyl-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2- b]pyran PM-N3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4] naphtho[1,2-b]pyranPM-O 3,3-di(4-methoxyphenyl)-6,11-dimethoxy-13-butyl-13-ethoxy-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran PM-P3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2- b]pyran PM-AA Anaphtho[1,2-b]pyran that exhibits a purple color when irradiated withultraviolet light. PM-BB A naphtho[1,2-b]pyran that exhibits ayellow-green color when irradiated with ultraviolet light.

EXAMPLE 1

The following materials were added in the order and the manner describedto a container suitable for use with a BRINKMAN PT-3000 homogenized:

Charge 1 Material Weight (grams) 2-Ethoxyethyl ether 50.0Tetrahydrofurfuryl alcohol 30.0 m-Methyl pyrrolidone 20.0 Hydroxylpropylcellulose 12.0 Silica 0.9

Charge 2 Material Weight Percent PM-D/PM-E/PM-B in 45/45/10 weight 1.65ratio TINUVIN ® 144 UV Stabilizer⁽¹⁾ 0.83 ⁽¹⁾Hindered amine ultravioletlight stabilizer available from CIBA Specialty Chemicals

Charge 1 was added to the container and mixed by the homogenizer at aspeed of 5000 rpm for 2 minutes or until the materials were dissolved.Charge 2 was added to the container and the resulting mixture was heatedwhile mixing until the materials dissolved.

EXAMPLE 2

The procedure of Example 1 was followed except that in Charge 2 thefollowing combination of photochromic materials was used:PM-A/PM-C/PM-D/PM-E/PM-G/PM-P in a weight ratio of 15/15/15/5/40/10.

EXAMPLE 3

The procedure of Example 1 was followed except that in Charge 2 thefollowing combination of photochromic materials was used:PM-A/PM-B/PM-C/PM-D/PM-H in a weight ratio of 10/20/20/30/20.

EXAMPLE 4

The procedure of Example 1 was followed except that in Charge 2 thefollowing combination of photochromic materials was used: PM-A/PM-C/PM-Iin a weight ratio of 25/45/30.

EXAMPLE 5

The procedure of Example 1 was followed except that in Charge 2 thefollowing combination of photochromic materials was used:PM-A/PM-C/PM-D/PM-E/PM-F in a weight ratio of 10/15/25/15/20.

EXAMPLE 6

The procedure of Example 1 was followed except that in Charge 2 thefollowing combination of photochromic materials was used:PM-A/PM-C/PM-D/PM-I/PM-J in a weight ratio of 30/24/20/13/13.

EXAMPLE 7

The procedure of Example 1 was followed except that in Charge 2 thefollowing photochromic material was used: PM-L.

EXAMPLE 8

The procedure of Example 1 was followed except that in Charge 2 thefollowing photochromic material was used: PM-K.

EXAMPLE 9

The procedure of Example 1 was followed except that in Charge 2 thefollowing combination of photochromic materials:PM-A/PM-C/PM-K/PM-AA/PM-BB in a weight ratio of 24/45/25/2/4 and 0.033percent by weight, based on the total weight of Charges 1 and 2, of D&CViolet #2 (CAS #81-48-1) were used.

EXAMPLE 10

The procedure of Example 1 was followed except that in Charge 2 thefollowing photochromic material was used: PM-M.

EXAMPLE 11

The procedure of Example 1 was followed except that in Charge 2 thefollowing photochromic material was used: PM-N.

EXAMPLE 12

The procedure of Example 1 was followed except that in Charge 2 thefollowing combination of photochromic materials was used:PM-A/PM-C/PM-I/PM-O/PM-AA/PM-BB in a weight ratio of 24/42/25/3/2/4.

COMPARATIVE EXAMPLE 1

The weight of the paper representing the area beneath the absorptionspectrum for Dye A in FIG. 1 of U.S. Pat. No. 6,102,543 was determinedas follows. FIG. 1 was enlarged 200 percent on a photocopier. The 410 nmpoint on the horizontal axis was established by determining that 100 nmequaled 39 mm and by marking the axis about 3.9 mm to the right of the400 nm point. The area on the enlarged figure beneath the spectrum from380 nm to 700 nm was cut out and weighed on a Mettler XA1200 balance.This was the total area weight. The area on the enlarged figure beneaththe spectrum from 410 nm to 700 nm was cutout and weighed. Thiscorresponded to the visible area weight. The weight of the area beneaththe spectrum from 380 to 410 nm was determined by subtracting thevisible area weight from the total area weight. The area weight percentof the spectrum in the visible region was calculated by dividing thevisible area weight by the total area weight and multiplying by 100. Thearea weight percent of the spectrum in the ultraviolet region wascalculated by dividing the ultraviolet area weight by the total areaweight and multiplying by 100. The results are listed in Table 3.

COMPARATIVE EXAMPLE 2

The procedure of Comparative Example 1 was followed except that theweight of the paper representing the area beneath the absorptionspectrum for Dye B in FIG. 1 of U.S. Pat. No. 6,102,543 was determined.

COMPARATIVE EXAMPLE 3

The procedure of Comparative Example 1 was followed except that theweight of the paper representing the area beneath the absorptionspectrum for Dye C in FIG. 1 of U.S. Pat. No. 6,102,543 was determined.

COMPARATIVE EXAMPLES 4–8

The commercially available plastic lenses described and listed belowwere used as Comparative Examples (CE). Each lens was a plano type lensthat reportedly activated to a grey or brown color as indicated. Eachlens was tested in duplicate and the average of the result was reportedhereinafter in Table 1.

CE # Lens Description Thickness 4A Corning SunSensors ® 1.8 mm (grey) 4BCorning SunSensors ® 1.8 mm (brown) 5A Hoya Hilux ® 2.0 mm (grey) 5BHoya Hilux ® 2.0 mm (brown) 6A Transitions ® Next 2.0 mm Generations(grey) 6B Transitions ® Next 2.0 mm Generations (brown) 7A Rodenstock ®ColorMatic 1.9 mm Extra (grey) 7B Rodenstock ® ColorMatic 1.9 mm Extra(brown) 8A Transitions ® III 1.50 2.0 mm (grey) 8B Transitions ® III1.50 2.0 mm (brown)

EXAMPLE 13

The Behind the Windshield Test and the Outdoor Test are describedherein. The preparation of samples is described in Part A, testing ofphotochromic performance is described in Part B, testing of percenttransmission is described in Part C and the spectra of representativeBWS photochromic materials compared to Comparative Examples 1–3 isdescribed in Part D.

Part A

Testing of Examples 1–12 was done with test samples prepared usingCR-607® monomer available from PPG Industries, Inc., with the additionof 0.02 weight percent Cyasorb® UV 5411, an ultraviolet light absorberfrom CIBA Specialty Chemicals Corp. and 2.5 parts per hundred of resin(pph) of diisopropyl peroxydicarbonate, a thermal initiator. Theinitiator and UV absorber were dissolved in the monomer by mixing andthen the monomer was poured into molds measuring 12 inches by 12 inchesby 0.08 inches (30.5 centimeters by 30.5 centimeters by 0.2centimeters). The molds were cured according to the following cycle.Hold for 6 hours at 36° C.; ramp up to 56° C. over 8 hours; after 2.0hours at 56° C., ramp up to 72° C.; after 8 hours, at 72° C. removesample and cool to 60° C. and demold.

Afterwards, the cured sheets were cut into two inch by two inch squares(5.08 centimeters by 5.08 centimeters). The test squares were washedwith dishwashing detergent and water, rinsed with deionized water andwiped with an acetone soaked tissue prior to the application of theexample solutions. The imbibition coating was applied to the testsamples by dispensing a quantity of imbibition coating on the testsample and spinning at about 1500 rpm for about four seconds to producea wet film-weight of 0.35 to 0.40 milligrams per lens. The resultingfilms were dried under an infrared light for about 20 minutes and placedin an oven at 135–140° C. for the times indicated in the followingtable. Afterward, the imbibed test samples were washed with soap andrinsed with water.

Example # Time 1, 2 and 5 4 hours 3, 4, and 6–12 8 hours

Part B

The photochromic imbibed test squares prepared in Part A were tested forphotochromic response in the Outdoor Test and the Behind the WindshieldTest as described herein on a Bench for Measuring Photochromics (BMP)optical bench made by Essilor, France.

The Behind the Windshield Test was used to determine the change inoptical density (ΔOD) obtained by the sample when tested underconditions simulating photochromic lens response on a wearer inside anautomobile. It was determined that the amount of light energy availableto activate a photochromic lens on a wearer in an automobile was 0.75Watts/m² integrated between 380 and 420 nm and 1.7 Klux (kilolumens/m²)whereas, the amount of energy available in the Outdoor Test was 6.7Watts/m² (UVA) integrated between 315 and 380 nm and 50 Klux. TheOutdoor Test was used to determine the change in optical densityobtained by the sample when tested under conditions simulatingphotochromic lens response on a wearer outdoors.

Prior to testing on the optical bench, the photochromic test squareswere conditioned by activating and fading as described hereinafter. Thetest squares were first exposed to 365 nanometer ultraviolet light forabout 10 minutes at a distance of about 14 centimeters to activate thephotochromic compounds. The UVA (315 to 380 nm) irradiance at the samplewas measured with a Licor Model Li-1800 spectroradiometer and found tobe 22.2 watts per square meter. The activated samples were then placedunder a 500 watt, high intensity halogen lamp for about 10 minutes at adistance of about 36 centimeters to bleach or inactivate thephotochromic compounds. The illuminance at the sample was measured withthe Licor spectroradiometer and found to be 21.4 Klux. The test squareswere then kept covered for at least 1 hour prior to testing on anoptical bench.

The BMP optical bench was fitted with two 150 watt Xenon arc lamps. Thelight path from Lamp 1 was directed through a 3 mm Schott KG-2 band-passfilter and appropriate neutral density filters that contributed to therequired UV and partial visible light irradiance level. The light pathfrom the Lamp 2 was directed through a 3 mm Schott KG-2 band-passfilter, a 400 nm cutoff filter and neutral density filters in order toprovide supplemental visible light illuminance. For the outdoor testconditions, both lamps were used, but for the in automobile simulation,only Lamp 1 with a direct irradiance path to the sample was used. Inthis irradiance path, the 3 mm Schott KG-2 band-pass filter and asimulated windshield typical of an auto windshield were used to controlthe irradiance spectral profile. Neutral density filters and voltagecontrol of the Xenon arc lamp were used to adjust the intensity of thelight.

The irradiance used for the Behind the Windshield Test was determined tobe an average radiant flux integrated between 380 and 420 nm of 0.75Watts/m² with 1.7 Klux of visible light. The samples were controlled ata temperature of 28° C. The outdoor simulated conditions were anirradiance level of 6.7 Watts/m² UVA, 50 Klux and controlled at atemperature of 23° C. The simulated windshield was prepared bylaminating a 0.73 mm thick piece of polyvinylbutyrate film from SolutiaInc. between two 2.3 mm thick layers of Solex 97 glass from PPGIndustries, Inc. The simulated windshield had a total thickness of 5.33mm. A spectra of the light passing through the simulated windshield asmeasured on the BMP is shown in FIG. 1.

Proprietary software was used on the BMP to control timing, irradiance,air cell and sample temperature, shuttering, filter selection andresponse measurement. A Zeiss spectrophotometer, Model MCS 501, withfiber optic cables for light delivery through the sample was used forresponse and color measurement. For single photochromic systems,response measurements were collected at the visible lambda max. Photopicresponse measurements were collected when testing multiple photochromiclens systems.

Response measurements, in terms of change in optical density (ΔOD) fromthe unactivated state to the activated or darkened state were determinedby establishing the initial unactivated transmittance, opening theshutter from the Xenon lamp(s) and measuring the transmittance duringactivation of the sample at selected intervals of time. Change inoptical density was determined according to the formula: ΔOD=log(% Tb/%Ta), where % Tb is the percent transmittance in the bleached state, % Tais the percent transmittance in the activated state and the logarithm isto the base 10. Optical density measurement can be per specificwavelength or photopic.

The Percent of the ΔOD retained by the test samples was determined bymeasuring the change in optical density (ΔOD) from the bleached to thedarkened state under conditions corresponding to outdoor simulation (OS)and behind the windshield (BWS) eyeglass wearer simulation. The examplesof the present invention and comparative examples were activated untilsaturated which was 15 minutes for the examples of the present inventionand 30 minutes for the comparative examples. The measure used was thepercent of ΔOD retained between the two conditions according to thefollowing formula:% ΔOD Retained=100×(ΔOD _(BWS) /ΔOD _(OS)).Results for Examples 1–12 are in Table 1 and the results for ComparativeExamples 4A/4B to 8A/8B are in Table 1A.

TABLE 1 ΔOD @ 15 min. ΔOD @ 15 min. % ΔOD Example # (OS) 23° C. (BWS)28° C. Retained 1 1.118 0.313 28 2 0.855 0.223 26 3 1.096 0.289 26 40.952 0.217 23 5 1.351 0.355 26 6 1.026 0.237 23 7 1.497 0.394 26 81.410 0.192 14 9 0.870 0.193 22 10 1.675 0.420 25 11 1.542 0.293 19 121.000 0.261 26

TABLE 1A ΔOD @ 30 min. ΔOD @ 30 min. % ΔOD Example # (OS) 23° C. (BWS)28° C. Retained CE-4A 0.545 0.008 1.5 CE-4B 0.566 0.019 3.4 CE-5A 0.5370.056 10 CE-5B 0.478 0.054 11 CE-6A 0.786 0.080 10 CE-6B 0.727 0.075 10CE-7A 0.583 0.043 7.4 CE-7B 0.484 0.036 7.4 CE-8A 0.576 0.040 6.9 CE-8B0.484 0.040 8.3

The results of Table 1 show that Examples 1–12, when der behind thewindshield eyeglass wearer simulating conditions, retained from 14 to 28percent of the ΔOD measured under outdoor simulating conditions, whereasin Table 1A, Comparative Examples 4A/B to 8A/B retained less than 12percent of the ΔOD measured under outdoor simulating conditions.

Part C

The photochromic test squares from Part A were conditioned by activatingand fading as described in Part B amd were tested for the percenttransmission through the sample unactivated bleached state under theoutdoor simulating (OS) condition of 23° C. and when activated under thebehind the windshield (BWS) eyeglass wearers simulating conditions at28° C. Testing was done using the BMP as described in Part B. Theresults are listed in Table 2.

TABLE 2 Bleached State % Activated State % Transmission TransmissionExample # (OS) 23° C. (BWS) 28° C. 1 82 39 2 86 52 3 84 44 4 82 44 5 8539 6 82 48 7 84 45 8 77 59 9 76 49 10  86 44 11  85 55 12  85 47 CE4A 8583 CE4B 85 82 CE5A 87 76 CE5B 86 76 CE6A 89 74 CE6B 89 75 CE7A 86 77CE7B 85 78 CE8A 87 79 CE8B 88 80

The results of Table 2 show that Examples 1–12 demonstrate an activatedstate luminous transmission at saturation of less than 60 percent.Comparative Examples 4A/4B to 8A/8B demonstrated an activated stateluminous transmission at saturation of greater than 60 percent.

Part D

The spectrum for each of Photochromic Materials: PM-A; PM-C; PM-D; PM-E;PM-F; PM-I and PM-J was prepared by dissolving enough of eachphotochromic material into a cuvette containing diethylene glycoldimethyl ether to result in a maximum absorbance of less than 1.0 asmeasured on a Cary Ultraviolet/Visible spectrophotometer, Model #3. Thefigure of absorbance versus wavelength for each photochromic materialwas printed at 100 percent. The 410 nm point on the horizontal axis wasestablished by determining that 20 nm equaled 6.0 mm and by marking thegraph 3.0 mm to the right of 400 nm. The paper representing the areabeneath the spectrum from 380 to 700 nm was cutout and weighed on aMettler XA1200 balance. This was the total area weight. The paperrepresenting the area beneath the spectrum between 380 and 410 nm wascutout and weighed. This corresponded to the UV area weight. The weightof the area beneath the spectrum from 410 to 700 nm was determined bysubtracting the ultraviolet area weight from the total area weight. Thearea weight percent of the spectrum in the UV region and visible regionwas calculated as done hereinbefore in Comparative Example 1. Theresults are listed in Table 3.

TABLE 3 TOTAL Area UV VISIBLE Weight % Weight % from Area Area of of380–700 from from UV Area VISIBLE nm 380–410 nm 410–700 nm of Area ofWeight Weight Weight TOTAL TOTAL Spectra (mg) (mg) (mg) Area Area PM-A30.2 27.7 2.5 92 8 PM-C 35.4 26.7 8.7 75 25 PM-D 35.4 25.2 10.2 71 29PM-E 29.5 23.1 6.4 78 22 PM-F 28.5 23.0 5.5 81 19 PM-I 27.4 23.0 4.4 8416 PM-J 29.3 24.5 4.8 84 16 PM-K 28.6 22.8 5.8 80 20 CE-1 16.1 4.6 11.529 71 CE-2 27.1 7.1 20.0 26 74 CE-3 71.0 6.6 64.4 9 91

The results of Table 3 show that each of the spectra of PhotochromicMaterials A, C, D, E, F, I, J and K had substantially more area in the380 to 410 nm ultraviolet wavelength range, than in the 410 to 700 nmvisible wavelength range. The results for the Comparative Examples 1through 3 showed substantially more area in the 410 to 700 nm visiblewavelength range than in the 380 to 410 nm ultraviolet wavelength range.

The present invention has been described with reference to specificdetails of particular embodiments thereof. It is not intended that suchdetails be regarded as limitations upon the scope of the inventionexcept insofar as to the extent that they are included in theaccompanying claims.

1. A photochromic article comprising: a) a substrate; and b) aphotochromic amount of at least one organic photochromic material (b)adapted to change from an unactivated form to an activated form byexposure to radiation substantially in the wavelength range from 380 to410 nanometers when measured over a range of from 380 to 700 nanometers,said photochromic article being adapted to retain at least 12 percent ofthe delta OD measured in the Outdoor Test when tested in the Behind theWindshield Test, said photochromic material (b) being represented by thefollowing graphic formula XIII:

 wherein, (aa) R₆₁ is represented by: (i) —SR₆₇, R₆₇ being chosen fromC₁–C₆ alkyl, aryl, mono- or di-substituted aryl, said aryl group beingphenyl or naphthyl and each of said aryl substituents being chosenindependently from C₁–C₆ alkyl, C₁–C₆ alkoxy or halogen; or (ii) anamino group chosen from: (1) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each beingindependently chosen from hydrogen, C₁–C₈ alkyl, aryl, furanyl,benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl,benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl,fluorenyl, C₁–C₈ alkylaryl, C₃–C₂₀ cycloalkyl, C₄–C₂₀ bicycloalkyl,C₅–C₂₀ tricycloalkyl or C₁–C₂₀ alkoxyalkyl and said aryl group beingphenyl or naphthyl; (2) a nitrogen containing ring represented by thefollowing graphic formula:

 wherein each Y being independently chosen for each occurrence from—CH₂—, —CH(R₂₆)—, —C(R₂₆)(R₂₆)—, —CH(aryl)—, —C(aryl)₂— or—C(R₂₆)(aryl)—; X being —Y—, —O—, —S—, —S(O)—, —S(O₂)—, —NH—, —N(R₂₆)—or —N(aryl)—; R₂₆ being C₁–C₆ alkyl; said aryl group being phenyl ornaphthyl, m being chosen from the integer 1, 2 or 3 and p being chosenfrom the integer 0, 1, 2 or 3; provided that when p is 0, X is Y; (3) agroup represented by one of the following graphic formulae:

wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen, C₁–C₅ alkyl, phenyl ornaphthyl; or the groups R₂₈ and R₂₉ together form a ring of 5 to 8carbon atoms; R₂₇ being chosen independently for each occurrence fromC₁–C₆ alkyl, C₁–C₆ alkoxy, fluoro or chloro and q being chosen from theinteger 0, 1 or 2; (4) unsubstituted, mono- or di-substituted C₄–C₁₈spirobicyclic amine; and (5) unsubstituted, mono- or di-substitutedC₄–C₁₈ spirotricyclic amine; said substituents for (4) and (5) beingindependently chosen for each occurrence from aryl, C₁–C₆ alkyl, C₁–C₆alkoxy or phenyl(C₁–C₆)alkyl; (bb) R₆₁′ is independently chosen for eachoccurrence from C₁–C₆ alkyl or C₁–C₆ alkoxy and q being chosen from theinteger 0, 1 or 2; (cc) R₆₂ and R₆₃ are each independently chosen from:(i) hydrogen, hydroxy, amino, mono- or di-substituted amino, C₁–C₁₂alkyl, C₃–C₁₂ alkylidene, C₂–C₁₂ alkylidyne, vinyl, C₃–C₇ cycloalkyl,C₁–C₆ alkoxyalkyl, allyl, benzyl, mono-substituted benzyl, chloro,fluoro or —C(O)W″, wherein W″ being hydroxy, C₁–C₆ alkyl, C₁–C₆ alkoxy,phenyl, mono-substituted phenyl, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, morpholino, piperidino or pyrrolidyl; said aminosubstituents in (cc)(i) being C₁–C₆ alkyl, phenyl, benzyl or naphthyl;each of said benzyl substituents being C₁–C₆ alkyl or C₁–C₆ alkoxy; (ii)an unsubstituted, mono- di- or tri-substituted group chosen from phenyl,naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl,thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl orindolyl; each of said group substituents in (cc)(ii) being chosenindependently for each occurrence from chloro, fluoro, C₁–C₆ alkyl orC₁–C₆ alkoxy; (iii) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being —(CH₂)_(r)— or—O—(CH₂)_(r)—, wherein r being chosen from the integer 1, 2, 3, 4, 5 or6, said substituent being connected to an aryl group which is a memberof another photochromic material; (iv) —OR_(67′), R_(67′) being chosenfrom C₁–C₆ alkyl, C₁–C₆ acyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkylsubstituted pheny(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substitutedphenyl(C₁–C₃)alkyl, C₁–C₆ alkoxy(C₂–C₆)alkyl, C₃–C₇ cycloalkyl,mono(C₁–C₄)alkyl substituted C₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, allyl, triarylsilyl, triarysilyloxy, tri(C₁–C_(C)₆)alkylsilyl, tri(C₁–C_(C) ₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyl,di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyl,di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyloxy, benzoyl, mono-substituted benzoyl,naphthoyl or mono-substituted naphthoyl; each of said benzoyl andnaphthoyl substituents being independently chosen from C₁–C₆ alkyl orC₁–C₆ alkoxy; or R_(67′) being —CH(R₆₈)Q″, wherein R₆₈ being chosen fromhydrogen or C₁–C₃ alkyl and Q″ being chosen from —CN, —CF₃, or COOR₆₈;R_(67′) being —C(O)V″, wherein V″ being chosen from hydrogen, C₁–C₆alkoxy, phenoxy, mono- or di-(C₁–C₆)alkyl substituted phenoxy, mono- ordi-(C₁–C₆)alkoxy substituted phenoxy, an unsubstituted, mono- ordi-substituted aryl group phenyl or naphthyl, amino,mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, phenylamino, mono- ordi-(C₁–C₆)alkyl substituted phenylamino, or mono- or di-(C₁–C₆)alkoxysubstituted phenylamino; each of said aryl group substituents beingindependently chosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (v) —CH(Q′″)₂,Q′″ being chosen from —CN or —COOR₆₉ and R₆₉ being chosen from hydrogen,C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl; each of said aryl group substituents being independentlychosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (vi) —CH(R₇₀)G″, R₇₀ beingchosen from hydrogen, C₁–C₆ alkyl or an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, and G″ being chosen from—COOR₆₉, —COR₇₁ or —CH₂OR₇₂, wherein R₇₁ being chosen from hydrogen,C₁–C₆ alkyl, an unsubstituted, mono- or di-substituted aryl group,phenyl or naphthyl, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino,phenylamino, mono- or di-(C₁–C₆)alkyl substituted phenylamino, mono- ordi-(C₁–C₆)alkoxy substituted phenylamino, diphenylamino, mono- ordi(C₁–C₆)alkyl substituted diphenylamino, mono- or di(C₁–C₆)alkoxysubstituted diphenylamino, morpholino or piperidino; R₇₂ being chosenfrom hydrogen, —C(O)R₆₉, C₁–C₆ alkyl, C₁–C₃ alkoxy(C₁–C₆)alkyl,phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl, each of said aryl group substituents being independentlychosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (vii) the group T wherein thegroup T is represented by the formula:-G[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′—[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′ wherein -G being chosen from—C(O)— or —CH₂—, G′ being chosen from C₁–C₃ alkoxy or a polymerizablegroup, x, y and z each being independently chosen from a number between0 and 50, and the sum of x, y and z being between 2 and 50; or (viii)R₆₂ and R₆₃ together form an oxo group or a substituted or unsubstitutedspiro-carbocyclic ring containing 3 to 6 carbon atoms or a substitutedor unsubstituted spiro-heterocyclic group containing 1 or 2 oxygen atomsand 3 to 6 carbon atoms including the spirocarbon atom, saidspiro-carbocyclic ring and spiro-heterocyclic group being annellatedwith 0, 1 or 2 benzene rings, said substituents being hydrogen or C₁–C₆alkyl; (dd) R₆₄ is hydrogen or C₁–C₆ alkyl; (ee) R₆₅ is hydrogen orC₁–C₆ alkyl; (ff) R₆₆ is chosen from hydrogen, C₁–C₆ alkyl or the groupR_(a) chosen from: (i) —OR₇₃, R₇₃ being chosen from phenyl(C₁–C₃)alkyl,C₁–C₆ alkyl, mono(C₁–C₆)alkyl substituted phenyl(C₁–C₃)alkyl,mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl, C₁–C₆alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl, mono(C₁–C₄)alkyl substituted C₃–C₇cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl, allyl or —CH(R₆₈)Q″described in (cc)(i); or (ii) an amino group being the same describedhereinbefore in (aa)(ii);

 and (gg) B and B′ are each independently chosen from (i)mono-T-substituted phenyl, wherein the group T is the same as describedhereinbefore in (cc)(vii); (ii) an unsubstituted, mono-, di-, ortri-substituted aryl group, phenyl or naphthyl; (iii) 9-julolidinyl orthe unsubstituted, mono- or di-substituted heteroaromatic group chosenfrom pyridyl furanyl, benzofuran-2yl, benzofuran-3yl, thienyl,benzothien-2yl, benzothien-3yl, dibenzofuranyl, dibenzothienyl,carbazoyl, benzopyridyl, indolinyl or fluorenyl, each of said aryl andheteroaromatic substituents in (hh)(ii) and (iii) being independentlychosen from hydroxy, —C(O)U, wherein U being hydroxy, C₁–C₆ alkyl, C₁–C₆alkoxy, phenyl, mono-substituted phenyl, amino, mono (C₁–C₆)alkylamino,di-(C₁–C₆)alkyklamino, morpholino, piperidino or pyrrolidyl; aryl,mono(C₁–C₆)alkoxyaryl, di(C₁C₆)alkoxyaryl, mono(C₁–C₆)alkylaryl,di(C₁–C₆)alkylaryl, chloroaryl, fluoroaryl, C₃–C₇ cycloalkylaryl, C₃–C₇cycloalkyl, C₃–C₇ cycloalkyloxy, C₃–C₇ cycloalkyloxy(C₁–C₆)alkyl, C₃–C₇cycloalkyloxy(C₁–C₆)alkoxy, aryl(C₁–C₆)alkyl, aryl(C₁–C₆)alkoxy,aryloxy, aryloxy(C₁–C₆)alkyl, aryloxy(C₁–C₆)alkoxy, mono- ordi-(C₁–C₆)alkylaryl(C₁–C₆)alkyl, mono- ordi-(C₁–C₆)alkoxyaryl(C₁–C₆)alkyl, mono- ordi-(C₁–C₆)alkylaryl(C₁–C₆)alkoxy, mono- or di-(C₁–C₆)alkoxy, amino,mono(C₁–C₆)alklamino di(C₁–C₆)alkylamino, diarylamino, piperazino,N-(C₁–C₆)alkypiperazino, N-arylpiperazino, aziridino, indolino,piperidino, morpholino, thiomorpholino, tetrahydroquinolino,tetrahydroisoquinolino, pyrrolidyl, C₁–C₆ alkyl, C₁–C₆ chloroalkyl,C₁–C₆ fluoroalkyl, C₁–C₆ alkoxy, mono(C₁–C₆)alkoxy(C₁–C₄)alkyl,acryloxy, methacryloxy, bromo, chloro or fluoro, said aryl being chosenfrom phenyl or naphthyl; (iv) an unsubstituted or mono-substituted groupchosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl,pyrrolinyl, phenothiazinyl, phenoxazinyl, phenazinyl or acridinyl, eachof said substituents being independently chosen from C₁–C₆ alkyl, C₁–C₆alkoxy, phenyl, fluoro, chloro or bromo; (v) a monosubstituted phenyl,said phenyl having a substituent located at the para position being—(CH₂)_(r)— or —O—(CH₂)_(r)—, wherein r being chosen from the integer 1,2, 3, 4, 5 or 6, said substituent being connected to an aryl group whichis a member of another photochromic material, and; (vi) a grouprepresented by one of the following graphic formulae:

 wherein A being independently chosen in each formula from methylene oroxygen and D being independently chosen in each formula from oxygen orsubstituted nitrogen, provided that when D is substituted nitrogen, A ismethylene; said nitrogen substituents being chosen from hydrogen, C₁–C₆alkyl, or C₂–C₆ acyl; each R₂₀ being independently chosen for eachoccurrence in each formula from C₁–C₆ alkyl, C₁–C₆ alkoxy, hydroxy,chloro or fluoro; R₁₈ and R₁₉ each being independently chosen in eachformula from hydrogen or C₁–C₆ alkyl; and q being chosen from theinteger 0, 1 or 2; (vii) C₁–C₆ alkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, C₁–C₆ alkoxy(C₁–C₆)alkyl, C₃–C₆ cycloalkyl,mono(C₁–C₆)alkoxy(C₃–C₆)cycloalkyl, mono(C₁–C₆)alkyl(C₃–C₆)-cycloalkyl,chloro(C₃–C₆)cycloalkyl, fluoro(C₃–C₆)cyclo-alkyl or C₄–C₁₂bicycloalkyl; (viii) a group represented by the following graphicformula:

 wherein L being chosen from hydrogen or C₁–C₄ alkyl and M being chosenfrom an unsubstituted, mono-, or di-substituted group chosen fromnaphthyl, phenyl, furanyl, or thienyl; each of said group substituentsbeing independently chosen from C₁–C₄ alkyl, C₁–C₄ alkoxy, fluoro, orchloro; or (ix) B and B′ taken together form fluoren-9-ylidene, mono-,or di-substituted fluoren-9-ylidene or a group being independentlychosen from saturated C₃–C₁₂ spiro-monocyclic hydrocarbon rings,saturated C₇–C₁₂ spiro-bicyclic hydrocarbon rings or saturated C₇–C₁₂spiro-tricyclic hydrocarbon rings; each of said fluoren-9-ylidenesubstituents being independently chosen from C₁–C₄ alkyl, C₁–C₄ alkoxy,fluoro or chloro.
 2. The photochromic article of claim 1 whereinphotochromic material (b) is represented by graphic formula XIIIwherein: (aa) R₆₁ is represented by: (i) —SR₆₇, R₆₇ being C₁–C₆ alkyl oraryl; or (ii) an amino group chosen from; (1) —N(R₁₆)R₁₇, R₁₆ and R₁₇each being independently chosen from C₁–C₈ alkyl, aryl, or C₃–C₂₀cycloalkyl; and said aryl group being phenyl or naphthyl; (2) a nitrogencontaining ring represented by the following graphic formula:

 wherein each Y being independently chosen for each occurrence from—CH₂—; X being —Y—, —O—, —S—, or —N(R₂₆)—; R₂₆ being C₁–C₆ alkyl; saidaryl group being phenyl or naphthyl, m being chosen from the integer 1,2 or 3 and p being chosen from the integer 0, 1, 2 or 3; provided thatwhen p is 0, X is Y; or (3) a group represented by one of the followinggraphic formulae:

wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen; R₂₇ being chosen independentlyfor each occurrence from C₁–C₆ alkyl, and q being chosen from theinteger 0, 1 or 2; (bb) R₆₁′ is independently chosen for each occurrencefrom C₁–C₆ alkyl or C₁–C₆ alkoxy and q being the integer 1; (cc) R₆₂ andR₆₃ are each independently chosen from: (i) hydrogen, hydroxy, C₁–C₁₂alkyl, C₃–C₁₂ alkylidene, C₃–C₇ cycloalkyl, or —C(O)W″, wherein W″ isC₁–C₆ alkoxy, mono(C₁–C₆)alkylamino or di(C₁–C₆)alkylamino; (ii) anunsubstituted, mono- di- or tri-substituted group chosen from phenyl;each of said group substituents in (c)(ii) being chosen independentlyfor each occurrence from chloro, fluoro, C₁–C₆ alkyl or C₁–C₆ alkoxy;(iii) a monosubstituted phenyl, said phenyl having a substituent locatedat the para position being —O—(CH₂)_(r)—, wherein r being chosen fromthe integer 3 or 6, said substituent being connected to an aryl groupwhich is a member of another photochromic material; (iv) —OR_(67′),R_(67′) being chosen from C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl,C₁–C₆)alkoxy(C₂–C₄)alkyl tri(C₁–C₆)alkylsilyl, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkylsilyloxy, di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyl,di(C₁–C₆)alkoxy(C₁–C₆)alkoyl)silyl or di(C₁–C₆)alkoxy(C₁–C₆alkyl)silyloxy; (v) —CH(Q′″)₂, Q′″ being chosen from —COOR₆₉ and R₆₉being C₁–C₆ alkyl; (vi) —CH(R₇₀)G″, R₇₀ being chosen from hydrogen,C₁–C₆ alkyl or an unsubstituted, mono- or di-substituted aryl group,phenyl or naphthyl, and G″ being chosen from —COOR₆₉, —COR₇₁ or—CH₂OR₇₂, wherein R₇₁ being chosen from hydrogen, C₁–C₆ alkyl, anunsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl,amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, phenylamino, mono- ordi-(C₁–C₆)alkyl substituted phenylamino, mono- or di-(C₁–C₆)alkoxysubstituted phenylamino, diphenylamino, mono- or di(C₁–C₆)alkylsubstituted diphenylamino, mono- or di-(C₁–C₆)alkoxy substituteddiphenylamino, morpholino or piperidino; R₇₂ being chosen from hydrogen,—C(O)R₆₉, C₁–C₆ alkyl, C₁–C₃ alkoxy(C₁–C₆)alkyl, phenyl(C₁–C₃)alkyl,mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl or an unsubstituted,mono- or di-substituted aryl group, phenyl or naphthyl, each of saidaryl group substituents being independently chosen from C₁–C₆ alkyl orC₁–C₆ alkoxy; or (vii) R₆₂ and R₆₃ together form an oxo group or asubstituted or unsubstituted spiro-carbocyclic ring containing 3 to 6carbon atoms or a substituted or unsubstituted spiro-heterocyclic groupcontaining 1 or 2 oxygen atoms and 3 to 6 carbon atoms including thespirocarbon atom, said spiro-carbocyclic ring and spiro-heterocyclicgroup being annellated with 0, 1 or 2 benzene rings, said substituentsbeing hydrogen or C₁–C₆ alkyl; (dd) R₆₄ is hydrogen or C₁–C₆ alkyl; (ee)R₆₅ is hydrogen or C₁–C₆ alkyl; (ff) R₆₆ is chosen from hydrogen, C₁–C₆alkyl or the group R_(a), said R_(a) chosen from: (i) —OR₇₃, R₇₃ beingchosen from phenyl(C₁–C₃)alkyl, C₁–C₆ alkyl, mono(C₁–C₆)alkylsubstituted phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substitutedphenyl(C₁–C₃)alkyl, C₁–C₆ alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl,mono(C₁–C₄)alkyl substituted C₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, allyl or —CH(R₆₈)Q″; or (ii) an amino group describedhereinbefore in (aa)(ii);

(gg) B and B′ are each independently chosen from: (i) an unsubstituted,mono-, di-, or tri-substituted phenyl group; (ii) a mono-substitutedheteroaromatic group chosen from benzofuran-2-yl, benzothien-3-yl,dibenzofuranyl, or carbazoyl; each of said phenyl and heteroaromaticsubstituents in (i) and (ii) being independently chosen from —C(O)U,wherein U being C₁–C₆ alkyl, C₁–C₆ alkoxy, mono-(C₁–C₆)alkylamino,di-(C₁–C₆)alkylamino, morpholino, or piperidino: or amino,mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, piperidino, mornholino orfluoro; (iii) an unsubstituted or mono-substituted phenothiazinyl, saidsubstituents being C₁–C₆ alkyl or C₁–C₆ alkoxy; (iv) a monosubstitutedphenyl, said phenyl having a substituent located at the para positionbeing —O—(CH₂)_(r)—, wherein r being chosen from the integer 3 or 6,said substituent being connected to an aryl group which is a member ofanother photochromic material; (v) a group represented by one of thefollowing graphic formulae:

 wherein A being independently chosen in each formula from methylene oroxygen and D being independently chosen in each formula from oxygen orsubstituted nitrogen, provided that when D is substituted nitrogen, A ismethylene; said nitrogen substituents being C₁–C₆ alkyl; each R₂₀ beingindependently chosen for each occurrence in each formula from C₁–C₆alkyl or C₁–C₆ alkoxy; R₁₈ and R₁₉ each being independently chosen ineach formula from hydrogen or C₁–C₆ alkyl; and q being chosen from theinteger 0, 1 or 2; (vi) C₁–C₆ alkyl, C₃–C₆ cycloalkyl, or C₄–C₁₂bicycloalkyl; (vii) a group represented by the following graphicformula:

 wherein L being hydrogen and M being an unsubstituted, mono-, ordi-substituted phenyl;  each of said group substituents beingindependently chosen from C₁C₄ alkoxy or fluoro; or (viii) B and B′taken together form fluoren-9-ylidene, mono-, or di-substitutedfluoren-9-ylidene or a saturated C₇–C₁₂ spiro-bicyclic hydrocarbonrings; each of said fluoren-9-ylidene substituents being fluoro.
 3. Thephotochromic article of claim 2 wherein photochromic material (b) ischosen from: (a)3,3-di(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(b)3-phenyl-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;(c)3,3-di(4-(2-methoxyethoxyphenyl))-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(d)3,3-di(4-methoxyphenyl)-11-morpholino-13-hydroxy-13-ethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(e)3,3-di(4-methoxyphenyl)-10-methoxy-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(f)3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-10-methoxy-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(g)3-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(h)3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;or (i)3,3-di(2-methoxyethoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran.4. The photochromic article of claim 1 further comprising at least oneother photochromic material (c) that is different from photochromicmaterial (b) wherein said photochromic material (c) is chosen from: (1)a photochromic material chosen from a fluoranthenoxazine represented bythe following graphic formula I:

 wherein, (a) R₁ is chosen from hydrogen, C₁–C₈ alkyl, C₃–C₇ cycloalkyl,phen(C₁–C₄)alkyl, naphth(C₁–C₄)alkyl, allyl, acrylyloxy(C₂–C₆)alkyl,methacrylyloxy(C₂–C₆)alkyl, C₂–C₄acyloxy(C₂–C₆)alkyl,carboxy(C₂–C₆)alkyl, cyano(C₂–C₆)alkyl, hydroxy(C₂–C₆)alkyl,triarylsilyl, triarylsilyloxy, tri(C₁–C₆)alkylsilyl,tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyl,di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyl,di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyloxy, C₁–C₆ alkoxy(C₂–C₄)alkyl or(C₂H₄O)_(r)—CH₃, wherein r is an integer from 1 to 6; (b) R₂ is chosenfrom C₁–C₅ alkyl, C₁–C₅ alkoxy, nitro, cyano, C₁–C₈ alkoxycarbonyl,C₁–C₄ acyloxy, halo, C₁–C₄ monohaloalkyl or C₁–C₄ polyhaloalkyl; saidhalo substituents being chloro, fluoro, iodo or bromo and q is 0, 1 or2; (c) R₃ and R₄ are each independently chosen from C₁–C₅ alkyl, benzyl,phenyl, mono- or di-substituted phenyl, said phenyl substituents beingC₁–C₅ alkyl or C₁–C₅ alkoxy; or R₃ and R₄ taken together form a groupchosen from a cyclic ring of from 5 to 8 carbon atoms which includes thespiro carbon atom; (d) R₅ is chosen from hydrogen, —CH₂Q and —C(O)W,wherein Q is halogen, hydroxy, benzoyloxy, C₁–C₆ alkoxy, C₂–C₆ acyloxy,amino, C₁–C₆ mono-alkylamino, C₁–C₆ dialkylamino, morpholino,piperidino, 1-indolinyl, pyrrolidyl, triarylsilyl, triarylsilyloxy,tri(C₁–C₆)alkylsilyl, tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyl,di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyl,di(C₁–C₆)alkoxy(C₁–C₆alkyl)silyloxy, or the group, —OCH(R₈)Z; W is thegroup, —OOH(R₈)Z, or an unsubstituted, mono-substituted, ordi-substituted heterocyclic ring containing 5 to 6 ring atoms, whichring includes as the hetero atom a nitrogen atom alone or one additionalhetero atom of nitrogen or oxygen; wherein Z is —CN, —CF₃, halogen,—C(O)R₈, or —COOR₈, R₈ is hydrogen or C₁–C₆ alkyl; said heterocyclicring substituents being chosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; or W is—OR₉ or —N(R₁₀)R₁₁, wherein R₉ is chosen from hydrogen, allyl, C₁–C₆alkyl, phenyl, mono(C₁–C₆)alkyl substituted phenyl,mono(C₁–C₆)alkoxy-substituted phenyl, phenyl(C₁–C₃)alkyl,mono(C₁–C₆)alkyl substituted phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxysubstituted phenyl(C₁–C₃)alkyl, C₁–C₆ alkoxy(C₂–C₄)alkyl, or C₁–C₆haloalkyl; and R₁₀ and R₁₁ are each independently chosen from hydrogen,C₁–C₆ alkyl, C₅–C₇cycloalkyl, phenyl, mono- or di-substituted phenyl, orR₁₀ and R₁₁ together with the nitrogen atom form a mono- ordi-substituted or unsubstituted heterocyclic ring containing from 5 to 6ring atoms, which ring includes as the hetero atom said nitrogen atomalone or one additional hetero atom of nitrogen or oxygen, said phenyland heterocyclic ring substituents being C₁–C₆ alkyl or C₁–C₆ alkoxy,and each of said halogen or halo groups in this part (d) being fluoro orchloro; (e) each R₆ and R₇ is independently chosen for each occurrencefrom aryl, mono(C₁–C₆)alkoxyaryl, di(C₁–C₆)alkoxyaryl,mono(C₁–C₆)alkylaryl, di(C₁–C₆)alkylaryl, bromoaryl, chloroaryl,fluoroaryl, C₃–C₇ cycloalkylaryl, C₃–C₇ cycloalkyl, C₃–C₇ cycloalkyloxy,C₃–C₇ cycloalkyloxy(C₁–C₆)alkyl, C₃–C₇ cycloalkyloxy(C₁–C₆)alkoxy,aryl(C₁–C₆)alkyl, aryl(C₁–C₆)alkoxy, aryloxy, aryloxy(C₁–C₆)alkyl,aryloxy(C₁–C₆)alkoxy, mono- or di(C₁–C₆)alkylaryl(C₁–C₆)alkyl, mono- ordi(C₁–C₆)alkoxyaryl(C₁–C₆)alkoxy, mono- ordi(C₁–C₆)alkylaryl(C₁–C₆)alkoxy, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, diarylamino, N—(C₁–C₆)alkylpiperazino,N-arylpiperazino, aziridino, indolino, piperidino, arylpiperidino,morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino,pyrryl, C₁–C₆ alkyl, C₁–C₆ bromoalkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, C₁–C₆ alkoxy, mono(C₁–C₆)alkoxy(C₁–C₄)alkyl, acryloxy,methacryloxy, bromo, chloro or fluoro; and q is independently chosen foreach occurrence form the integer 0, 1, or 2; (2) a photochromic materialchosen from a naphthopyran represented by the following graphic formulaII:

 wherein: (a) R₁₂ is hydrogen or a C₁–C₆ alkyl; (b) R₁₃ is hydrogen orthe group, —C(O)J, J being —OR₁₅ or —N(R₁₀)R₁₁, wherein R₁₅ is hydrogen,allyl, C₁–C₆ alkyl, phenyl, C₁–C₆ monoalkyl substituted phenyl, C₁–C₆monoalkoxy substituted phenyl, phenyl(C₁–C₃)alkyl, C₁–C₆ monoalkylsubstituted phenyl(C₁–C₃)alkyl, C₁–C₆ monoalkoxy substitutedphenyl(C₁–C₃)alkyl, C₁–C₆ alkoxy(C₂–C₄)alkyl, or C₁–C₆ monohaloalkyl,and wherein R₁₀ and R₁₁ are the same as described hereinbefore in(1)(d), and said halo substituent being chloro or fluoro; (c) R₁₄ is—OR₉, —N(R₁₀)R₁₁, wherein R₉, R₁₀ and R₁₁ are the same as describedhereinbefore in (1)(d), or the group, —C(O)V; wherein V is C₁–C₆ alkyl,phenyl, C₁–C₆ mono- or C₁–C₆ di-alkyl substituted phenyl, C₁–C₆ mono- orC₁–C₆ di-alkoxy substituted phenyl, C₁–C₆ alkoxy, phenoxy, C₁–C₆ mono-or C₁–C₆ di-alkyl substituted phenoxy, C₁–C₆ mono- or C₁–C₆ di-alkoxysubstituted phenoxy, C₁–C₆ alkylamino, phenylamino, C₁–C₆ mono- or C₁–C₆di-alkyl substituted phenylamino, or C₁–C₆ mono- or C₁–C₆ di-alkoxysubstituted phenylamino, and said halo substituent being chloro, fluoroor bromo, provided that either R₁₂ or R₁₃ is hydrogen; and (d) B and B′are each independently chosen from: (i) mono-T-substituted phenyl,wherein the group T is represented by the formula:-G[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′—[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′ wherein -G being chosen from—C(O)— or —CH₂—, G′ being chosen from C₁–C₃ alkoxy or a polymerizablegroup, x, y and z each being independently chosen from a number between0 and 50, and the sum of x, y and z being between 2 and 50; (ii) anunsubstituted, mono-, di-, or tri-substituted aryl group, phenyl ornaphthyl; (iii) 9-julolidinyl or the unsubstituted, mono- ordi-substituted heteroaromatic group chosen from pyridyl furanyl,benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl,benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl,benzopyridyl, indolinyl or fluorenyl, each of said aryl andheteroaromatic substituents in (ii) and (iii) being independently chosenfrom hydroxy, —C(O)U, wherein U being hydroxy, C₁–C₆ alkyl, C₁–C₆alkoxy, phenyl, mono-substituted phenyl, amino, mono (C₁–C₆)alkylamino,di-(C₁–C₆)alkylamino, morpholino, piperidino or pyrrolidyl; aryl,mono(C₁–C₆)alkoxyaryl, di(C₁–C₆)alkoxyaryl, mono(C₁–C₆)alkylaryl,di(C₁–C₆)alkylaryl, chloroaryl, fluoroaryl, C₃–C₇ cycloalkylaryl, C₃–C₇cycloalkyl, C₃–C₇ cycloalkyloxy, C₃–C₇ cycloalkyloxy(C₁–C₆)alkyl, C₃–C₇cycloalkyloxy(C₁–C₆)alkoxy, aryl(C₁–C₆)alkyl, aryl(C₁–C₆)alkoxy,aryloxy, aryloxy(C₁–C₆)alkyl, aryloxy(C₁–C₆)alkoxy, mono- ordi-(C₁–C₆)alkylaryl(C₁–C₆)alkyl, mono- ordi-(C₁–C₆)alkoxyaryl(C₁–C₆)alkyl, mono- ordi-(C₁–C₆)alkylaryl(C₁–C₆)alkoxy, mono- ordi-(C₁–C₆)alkoxyaryl(C₁–C₆)alkoxy, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, diarylamino, piperazino, N-(C₁–C₆)alkylpiperazino,N-arylpiperazino, aziridino, indolino, piperidino, morpholino,thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl,C₁–C₆ alkyl, C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl, C₁–C₆ alkoxy,mono(C₁–C₆)alkoxy(C₁–C₄)alkyl, acryloxy, methacryloxy, bromo, chloro orfluoro, said aryl being chosen from phenyl or naphthyl; (iv) anunsubstituted or mono-substituted group chosen from pyrazolyl,imidazolyl, pyrazolinyl, imidazolinyl, pyrrolinyl, phenothiazinyl,phenoxazinyl, phenazinyl or acridinyl, each of said substituents beingindependently chosen from C₁–C₆ alkyl, C₁–C₆ alkoxy, phenyl, fluoro,chloro or bromo; (v) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being —(CH₂)_(r)— or—O—(CH₂)_(r)—, wherein r being chosen from the integer 1, 2, 3, 4, 5 or6, said substituent being connected to an aryl group which is a memberof another photochromic material, and; (vi) a group represented by oneof the following graphic formulae:

 wherein A being independently chosen in each formula from methylene oroxygen and D being independently chosen in each formula from oxygen orsubstituted nitrogen, provided that when D is substituted nitrogen, A ismethylene; said nitrogen substituents being chosen from hydrogen, C₁–C₆alkyl, or C₂–C₆ acyl; each R₂₀ being independently chosen for eachoccurrence in each formula from C₁–C₆ alkyl, C₁–C₆ alkoxy, hydroxy,chloro or fluoro; R₁₈ and R₁₉ each being independently chosen in eachformula from hydrogen or C₁–C₆ alkyl; and q being chosen from theinteger 0, 1 or 2; (vii) C₁–C₆ alkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, C₁–C₆ alkoxy(C₁–C₄)alkyl, C₃–C₆ cycloalkyl,mono(C₁–C₆)alkoxy(C₃–C₆)cycloalkyl, mono(C₁–C₆)alkyl(C₃C₆)-cycloalkyl,chloro(C₃–C₆)cycloalkyl, fluoro(C₃–C₆)cyclo-alkyl or C₄–C₁₂bicycloalkyl; (viii) a group represented by the following graphicformula:

 wherein L being chosen from hydrogen or C₁–C₄ alkyl and M being chosenfrom an unsubstituted, mono-, or di-substituted group chosen fromnaphthyl, phenyl, furanyl, or thienyl; each of said group substituentsbeing independently chosen from C₁–C₄ alkyl, C₁–C₄ alkoxy, fluoro, orchloro; or (ix) B and B′ taken together form fluoren-9-ylidene, mono-,or di-substituted fluoren-9-ylidene or a group being independentlychosen from saturated C₃–C₁₂ spiro-monocyclic hydrocarbon rings,saturated C₇–C₁₂ spiro-bicyclic hydrocarbon rings or saturated C₇–C₁₂spiro-tricyclic hydrocarbon rings; each of said fluoren-9-ylidenesubstituents being independently chosen from C₁–C₄ alkyl, C₁–C₄ alkoxy,fluoro or chloro; (3) a photochromic material chosen from a naphthopyranrepresented by the following graphic formula III:

 wherein, (a) R₂₁ is the group, —C(O)W or CH₂Q, described hereinbeforein (1)(d); (b) R₂₂ and each R₂₃ are independently chosen for eachoccurrence from hydroxy, NH₂ or N(R)H; wherein R is C₁–C₆ alkyl or aryland n is chosen from the integers 0, 1, 2, or 3; (c) B and B′ are eachindependently chosen from the groups described hereinbefore in (2)(d);(4) a photochromic material chosen from a naphthopyran represented bythe following graphic formula IV:

 wherein, (a) R₅ is the same group described hereinbefore in (1) (d);(b) R₂₄ and R₂₅ are each chosen from hydrogen or an amino group definedhereinafter, provided that R₂₄ and R₂₅ are not both hydrogen; said aminogroup being: (i) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each being independently chosenfrom hydrogen, C₁–C₈ alkyl, aryl, furanyl, benzofuran-2-yl,benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl,dibenzofuranyl, dibenzothienyl, benzopyridyl, fluorenyl, C₁–C₈alkylaryl, C₃–C₂₀ cycloalkyl, C₄–C₂₀ bicycloalkyl, C₅–C₂₀ tricycloalkylor C₁–C₂₀ alkoxyalkyl and said aryl group being phenyl or naphthyl; (ii)a nitrogen containing ring represented by the following graphic formula:

 wherein each Y being independently chosen for each occurrence from—CH₂—, —CH(R₂₆)—, —C(R₂₆)(R₂₆)—, —CH(aryl)-, —C(aryl)₂— or—C(R₂₆)(aryl)-; X being —Y—, —O—, —S—, —S(O)—, —S(O₂)—, —NH—, —N(R₂₆)—or —N(aryl)-; R₂₆ being C₁–C₆ alkyl; said aryl group being phenyl ornaphthyl, m being chosen from the integer 1, 2 or 3 and p being chosenfrom the integer 0, 1, 2 or 3; provided that when p is 0, X is Y; (iii)a group represented by one of the following graphic formulae:

 wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen, C₁–C₅ alkyl, phenyl ornaphthyl; or the groups R₂₈ and R₂₉ together form a ring of 5 to 8carbon atoms; R₂₇ being chosen independently for each occurrence fromC₁–C₆ alkyl, C₁–C₆ alkoxy, fluoro or chloro and q being chosen from theinteger 0, 1 or 2; (iv) unsubstituted, mono- or di-substituted C₄–C₁₈spirobicyclic amine; or (v) unsubstituted, mono- or di-substitutedC₄–C₁₈ spirotricyclic amine; said substituents for (iv) and (v) beingindependently chosen for each occurrence from aryl, C₁–C₆ alkyl, C₁–₆alkoxy or phenyl(C₁–C₆)alkyl; (c) B and B′ are each independently chosenfrom the groups described hereinbefore in (2)(d); (5) a photochromicmaterial chosen from a phenanthropyran represented by one of thefollowing graphic formula VA or VB:

 wherein, (a) R₃₁ is the group R₅, described hereinbefore in (1)(d); (b)R₃₂ is hydrogen, C₁–C₆ alkyl, C₁–C₆ alkoxy, C₃–C₇ cycloalkyl, pyridyl,phenyl, mono-substituted or di-substituted phenyl, said phenylsubstituents being C₁–C₆ alkyl, C₁–C₆ alkoxy, hydroxy, amino, chloro, orfluoro; (c) each R₃₃ is independently chosen for each occurrence fromchloro, fluoro, amino, C₁–C₆ monoalkylamino, —N(R₁₀)R₁₁, which wasdescribed hereinbefore in (1)(d), phenyl, C₁–C₆ alkyl, or —OR₃₄, whereinR₃₄ is hydrogen, C₁–C₆ alkyl, allyl, or acetyl, and q is the integer 0,1, or 2; and (d) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (2)(d); (6) a photochromic material chosenfrom a fluoranthenopyran represented by the following graphic formulaVI:

 wherein, (a) R₃₅ and R₃₆ are each independently chosen for eachoccurrence from hydroxy, aryl, mono(C₁–C₆)alkoxyaryl,di(C₁–C₆)alkoxyaryl, mono(C₁–C₆)alkylaryl, di(C₁–C₆)alkylaryl,bromoaryl, chloroaryl, fluoroaryl, C₃–C₇ cycloalkylaryl, C₃–C₇cycloalkyl, C₃–C₇ cycloalkyloxy, C₃–C₇ cycloalkyloxy(C₁–C₆)alkyl, C₃–C₇cycloalkyloxy(C₁–C₆)alkoxy, aryl(C₁–C₆)alkyl, aryl(C₁–C₆)alkoxy,aryloxy, aryloxy(C₁–C₆)alkyl, aryloxy(C₁–C₆)alkoxy, mono- ordi(C₁–C₆)alkylaryl(C₁–C₆)alkyl, mono- anddi(C₁–C₆)alkoxyaryl(C₁–C₆)alkyl, mono- ordi(C₁–C₆)alkylaryl(C₁–C₆)alkoxy, mono- ordi(C₁–C₆)alkoxyaryl(C₁–C₆)alkoxy, C₁–C₆ alkyl, C₁–C₆ bromoalkyl, C₁–C₆chloroalkyl, C₁–C₆ fluoroalkyl, C₁–C₆ alkoxy,mono(C₁–C₆)alkoxy(C₁–C₄)alkyl, acryloxy, methacryloxy, bromo, chloro,fluoro, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, phenylamino,mono- or di-(C₁–C₆)alkyl substituted phenylamino or mono- ordi-(C₁–C₆)alkoxy substituted phenylamino, and q is the integer 0, 1 or2; (b) R₅ is chosen from the group described hereinbefore in (1)(d); and(c) B and B′ are each independently chosen from the groups describedhereinbefore in (2)(d); (7) a photochromic material chosen from anaphthopyran represented by the following graphic formula VII:

 wherein, (a) R₃₇ and R₃₈ together form an oxo group or R₃₇ and R₃₈ eachare independently chosen for each occurrence from hydrogen, C₁–C₆ alkyl,C₃–C₇ cycloalkyl, allyl, phenyl, mono- or di-substituted phenyl, benzyl,mono-substituted benzyl, naphthyl, mono- or di-substituted naphthyl,C₄–C₁₂ bicycloalkyl, linear or branched C₃–C₁₂ alkenyl, C₁–C₆ alkoxycarbonyl(C₁–C₆)alkyl, methacryloxy(C₁–C₆)alkyl, acryloxy(C₁–C₆)alkyl,C₁–C₄ acyloxy(C₁–C₆)alkyl, C₁–C₆ alkoxy(C₁–C₆)alkyl or theunsubstituted, mono- or di-substituted heteroaromatic groups pyridyl,furanyl, benzofuran-2-yl, benzyfuran-3-yl, thienyl, benzothien-2-yl,benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazolyl,benzopyridyl and indolyl, each of said phenyl, benzyl, naphthyl andheteroaromatic group substituents being C₁–C₆ alkyl, C₁–C₆ alkoxy,morpholino, di(C₁–C₆)alkylamino, chloro or fluoro; (b) R₃₉ is chosenfrom C₁–C₆ alkyl, C₁–C₆ alkoxy, chloro, fluoro, phenyl, mono- anddi-substituted phenyl, benzyl or mono-substituted benzyl, C₃–C₇cycloalkyl, aryloxy, di(C₁–C₆)alkylamino, morpholino, thiomorpholino,piperidino, pyridyl, tetrahydroquinolino, isoquinolino, aziridino,diarylamino, N—(C₁–C₆)alkyl piperizino or N-aryl piperizino, wherein thearyl groups are phenyl or naphthyl, each of said phenyl and benzylsubstituents being C₁–C₆ alkyl, C₁–C₆ alkoxy, fluoro or chloro, and q isthe integer 0, 1 or 2; (c) I is oxygen or —N(R₄₀)—, wherein R₄₀ ishydrogen, C₁–C₆ alkyl, C₃–C₇ cycloalkyl, allyl, vinyl, C₁–C₅ acyl,phenyl, mono- or di-substituted phenyl, benzyl, mono-substituted benzyl,C₁–C₄ alkoxycarbonyl(C₁–C₆)alkyl, methacryloxy(C₁–C₆)alkyl,acryloyloxy(C₁–C₆)alkyl, phenyl(C₁–C₆)alkyl, naphthyl, C₄–C₁₂bicycloalkyl, C₂–C₄ acyloxy or the unsubstituted or substitutedheteroaromatic groups pyridyl, furanyl, benzofuran-2-yl,benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl,dibenzofuranyl, dibenzothienyl, carbazolyl, benzopyridyl or indolyl,each of said phenyl, benzyl and heteroaromatic group substituents beingC₁–C₆ alkyl or C₁–C₆ alkoxy; (d) K is oxygen, —N(R₄₀)— or —C(R₄₁)(R₄₂)—,wherein R₄₁ and R₄₂ are each hydrogen, C₁–C₆ alkyl or C₃–C₇ cycloalkyl;and (e) B and B′ are each independently chosen from the groups describedhereinbefore in (2)(d); (8) a photochromic material chosen from anaphthopyran represented by the following graphic formula VIII:

 wherein, (a) R₄₃ and R₄₄ together form an oxo group or R₄₃ and R₄₄ areboth hydrogen, C₁–C₆ alkyl, C₃–C₇ cycloalkyl, allyl, phenyl,mono-substituted phenyl, benzyl or mono-substituted benzyl each of saidphenyl and benzyl group substituents being C₁–C₆ alkyl or C₁–C₆ alkoxy;(b) R₄₅ is hydrogen, C₁–C₆ alkyl, C₃–C₇ cycloalkyl, or the group,CH(B)B′, wherein B and B′ are each independently chosen from the groupsdescribed hereinbefore in (2)(d); (c) R₄₆ is hydrogen, C₁–C₆ alkyl, orC₃–C₇ cycloalkyl; (d) each R₄₇ is C₁–C₆ alkyl, C₁–C₆ alkoxy, chloro orfluoro, and q is the integer 0, 1, or 2; and (e) B and B′ are eachindependently chosen from the groups described hereinbefore in (2)(d);(9) a photochromic material chosen from a naphthopyran represented bythe following graphic formulae IXA, IXB, IXC, IXD, IXE, IXF, IXG or IXH:

 wherein, (a) R₄₃ and R₄₄ are the same groups described hereinbefore in(8)(a); (b) each R₄₇ and q are the same as described hereinbefore in(8)(d); and (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (2)(d); (10) a photochromic material chosenfrom a naphthopyran represented by the following graphic formulae XA orXB:

 wherein, (a) A′ is chosen from: (i) an unsubstituted, mono-substitutedor di-substituted heterocyclic ring chosen from benzothieno, benzofuranoor indolo, the 2,3 or 3,2 positions of said heterocyclic ring beingfused to the i, j or k side of said naphthopyran represented by graphicformula XA or said heterocyclic ring is fused to the f side of saidnaphthopyran represented by graphic formula XB; or (ii) anunsubstituted, mono-substituted or di-substituted indeno group fused tothe i, j or k side of said naphthopyran represented by graphic formulaXA or to the f side of said naphthopyran represented by graphic formulaXB; each of said heterocyclic ring and indeno group substituents beingC₁–C₆ alkyl, C₅–C₇ cycloalkyl, C₁–C₆ alkoxy, —N(R₁₀)R₁₁, which wasdescribed hereinbefore in (1)(d), chloro, fluoro, benzo, mono- ordi-substituted benzo group fused to the benzo portion of thebenzothieno, benzofurano, indeno or indolo moiety, said benzosubstitutent being C₁–C₆ alkyl, C₅–C₇ cycloalkyl, C₁–C₆ alkylmono-substituted (C₅–C₇)cycloalkyl, C₁–C₆ alkoxy, —N(R₁₀)R₁₁, which wasdescribed hereinbefore in (1) (d), chloro or fluoro; (b) R₄₈ is chosenfrom: (i) —C(O)W′, W′ being —OR₉ or —N(R₁₀)R₁₁, wherein said groups weredescribed hereinbefore in (1)(d); or (ii) —C(R₅₁)₂X′, wherein X′ is —CN,chloro, fluoro, hydroxy, benzoyloxy, C₁–C₆ alkoxy, C₂–C₆ acyloxy, amino,C₁–C₆ mono-alkylamino, C₁–C₆ dialkylamino, morpholino, piperidino,1-indolinyl, pyrrolidyl, or trimethylsilyloxy, R₅₁ is hydrogen, C₁–C₆alkyl, phenyl or naphthyl, and each of said phenyl and heterocyclic ringsubstituents in this part (b)(i) and (ii) being C₁–C₆ alkyl or C₁–C₆alkoxy; (c) R₄₉ is hydrogen, C₁–C₆ alkyl, the mono-, di- ortri-substituted aryl groups phenyl or naphthyl, said aryl substituentsbeing C₁–C₆ alkyl, C₁–C₆ alkoxy, chloro or fluoro; or (d) each R₅₀ ischloro, fluoro, C₁–C₆ alkyl, C₁–C₆ alkoxy, phenyl, naphthyl, phenoxy,naphthoxy or the group, —N(R₁₀)R₁₁, described hereinbefore in (1)(d),and q is selected from the integers 0, 1 or 2 in said naphthopyranrepresented by graphic XA, or each R₅₀ is chloro, fluoro, phenoxy,naphthoxy or the group, —N(R₁₀)R₁₁, and p is selected from the integers0, 1, 2 or 3 in said naphthopyran represented by graphic formula XB; and(e) B and B′ are each independently chosen from the groups describedhereinbefore in (2)(d); (11) a photochromic material chosen from aindenonaphthopyran represented by the following graphic formulae XIA orXIB:

 wherein, (a) A″ is an unsubstituted, mono-substituted or di-substitutedheterocyclic ring chosen from furo, thieno, benzothieno, benzofurano orindolo, the 2,3 or 3,2 positions of said heterocyclic ring being fusedto the g, h or i side of XIB or to the n, o or p side of XIA, saidheterocyclic ring substituents being C₁–C₆ alkyl, C₅–C₇ cycloalkyl,C₁–C₆ alkoxy, chloro or fluoro; (b) R₅₂ and R₅₃ together form an oxogroup, a spiro heterocyclic group having 2 oxygen atoms and from 3 to 6carbon atoms including the spirocarbon atom, or R₅₂ and R₅₃ are eachhydrogen, hydroxy, C₁–C₆ alkyl, C₃–C₇cycloalkyl, allyl, phenyl,mono-substituted phenyl, benzyl, mono-substituted benzyl, chloro, fluoroor the group, —C(O)W″, wherein each W″ is hydroxy, C₁–C₆ alkyl, C₁–C₆alkoxy, phenyl, mono-substituted phenyl, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, morpholino, piperidino or pyrrolidyl; or R₅₂ andR₅₃ are each the group, the group, —N(R₁₀)R₁₁, described hereinbefore in(1)(d), or —OR₅₄, wherein each R₅₄ is C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl,mono(C₁–C₆)alkyl substituted phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxysubstituted phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substitutedphenyl(C₁–C₃)alkyl, C₁–C₆ alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl,mono(C₁–C₄)alkyl substituted C₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, allyl, the group, —CH(R₅₅)X″, wherein each R₅₅ is hydrogenor C₁–C₃ alkyl, each X″ is —CN, —CF₃, or —COOR₅₅, or each R₅₄ is thegroup, —C(O)Y″, wherein each Y′ is hydrogen, C₁–C₆ alkyl, C₁–C₆ alkoxy,the unsubstituted, mono- or di-substituted aryl groups, phenyl ornaphthyl, phenoxy, mono- or di-(C₁–C₆)alkyl substituted phenoxy, mono-or di-(C₁–C₆)alkoxy substituted phenoxy, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, phenylamino, mono- or di-(C₁–C₆)alkyl substitutedphenylamino or mono- or di-(C₁–C₆)alkoxy substituted phenylamino, eachof said phenyl, benzyl or aryl group substituents being C₁–C₆ alkyl orC₁–C₆ alkoxy; (c) each R₄₇ and q are the same as described hereinbeforein (8)(d); and (d) B and B′ are each independently chosen from thegroups described hereinbefore in (2)(d); (12) a photochromic materialchosen from an indenonaphthopyran represented by graphic formulae XIIAor XIIB wherein:

(a) A″ is the same group as described hereinbefore in (11)(a) wherein A″is fused to the g, h or i side of XIIB or to the n, o or p side of XIIA;(b) R₅₆ is hydrogen, hydroxy, bromo, fluoro or chloro and R₅₇ is thegroup, —CH(V′)₂, wherein V′ is —CN or —COOR₅₈, and each R₅₈ is hydrogen,C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl orthe unsubstituted, mono- or di-substituted aryl groups phenyl ornaphthyl, or R₅₇ is the group, —CH(R₅₉)Y″, wherein R₅₉ is hydrogen,C₁–C₆ alkyl or the unsubstituted, mono- or di-substituted aryl groupsphenyl or naphthyl, and Y″ is —COOR₅₈, —COR₅₉, or —CH₂OR₆₀, wherein R₅₉is hydrogen, C₁–C₆ alkyl, the unsubstituted, mono- or di-substitutedaryl groups phenyl or naphthyl, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, phenylamino, mono-or di-(C₁–C₆)alkyl substitutedphenylamino, mono- or di-(C₁–C₆)alkoxy substituted phenylamino,diphenylamino, mono- or di-(C₁–C₆)alkyl substituted diphenylamino, mono-or di-(C₁–C₆)alkoxy substituted diphenylamino, morpholino, orpiperidino; R₆₀ is hydrogen, —COR₅₈, C₁–C₆ alkyl, C₁–C₃alkoxy(C₁–C₆)alkyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl, orthe unsubstituted, mono- or di-substituted aryl groups phenyl ornaphthyl, each of said aryl group substituents being C₁–C₆ alkyl orC₁–C₆ alkoxy; or (c) R₅₆ and R₅₇ together form the group, ═C(V′)₂ or═C(R₅₉)W′″, wherein W′″ is —COOR₅₈ or —COR₅₉; (d) each R₄₇ and q are thesame as described hereinbefore in (8) (d); and (e) B and B′ are eachindependently chosen fromthe groups described hereinbefore in (2)(d);(13) a photochromic material chosen from an indenonaphthopyranrepresented by the following graphic formula XIV:

 wherein, (a) R₇₄ and R₇₅ are each independently chosen from: (i)hydrogen, hydroxy, amino, mono- or di-substituted amino, C₁–C₁₂ alkyl,C₃–C₁₂ alkylidene, C₂–C₁₂ alkylidyne, vinyl, C₃–C₇ cycloalkyl, C₁–C₆alkoxyalkyl, allyl, benzyl, mono-substituted benzyl, chloro, fluoro or—C(O)W″, wherein W″ is hydroxy, C₁–C₆ alkyl, C₁–C₆ alkoxy, phenyl,mono-substituted phenyl, amino, mono(C₁–C₆ alkyl amino, di(C₁–C₆)alkylamino, morpholino, piperidino or pyrrolidyl; said amino substituents in(a)(i) being C₁–C_(C) ₆ alkyl, phenyl, benzyl or naphthyl; each of saidbenzyl substituents being C₁–C₆ alkyl or C_(1–C) ₆ alkoxy; (ii) anunsubstituted, mono- di- or tri-substituted group chosen from phenyl,naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl,thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl orindolyl; each of said group substituents in (a)(ii) being chosenindependently for each occurrence from chloro, fluoro, C₁–C₆ alkyl orC₁–C₆ alkoxy; (iii) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being as described hereinbeforein (2)(d)(v); (iv) —OR_(67′), R_(67′) being chosen from C₁–C₆ alkyl,C₁–C₆ acyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl,C₁–C₆ alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl, mono(C₁–C₄)alkyl substitutedC₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl, allyl,triarylsilyl, triarylsilyloxy, tri(C₁–C₆)alkylsilyl,tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ aloxy)silyl,di(C₁–C₆)alkyl(C₁–C₆ aloxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyl,di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyloxy, benzoyl, mono-substituted benzoyl,naphthoyl or mono-substituted naphthoyl; each of said benzoyl andnaphthoyl substituents being independently chosen from C₁–C₆ alkyl orC₁–C₆ alkoxy; or R_(67′) being —CH(R₆₈)Q″, wherein R₆₈ being chosen fromhydrogen or C₁–C₃ alkyl and Q″ being chosen from —CN, —CF₃, or —COOR₆₈;or R_(67′) being —C(O)V″, wherein V″ being chosen from hydrogen, C₁–C₆alkoxy, phenoxy, mono- or di-(C₁–C₆)alkyl substituted phenoxy, mono- ordi-(C₁–C₆)alkoxy substituted phenoxy, an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, amino,mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, phenylamino, mono- ordi-(C₁–C₆)alkyl substituted phenylamino, or mono- or di-(C₁–C₆)alkoxysubstituted phenylamino; each of said aryl group substituents beingindependently chosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (v) —CH(Q′″)₂,Q′″ being chosen from —CN or —COOR₆₉ and R₆₉ being chosen from hydrogen,C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl; each of said aryl group substituents being independentlychosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (vi) —CH(R₇₀)G″, R₇₀ beingchosen from hydrogen, C₁–C₆ alkyl or an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, and G″ being chosen from—COOR₆₉, —COR₇₁ or —CH₂OR₇₂, wherein R₇₁ being chosen from hydrogen,C₁–C₆ alkyl, an unsubstituted, mono- or di-substituted aryl group,phenyl or naphthyl, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino,phenylamino, mono- or di-(C₁–C₆)alkyl substituted phenylamino, mono- ordi-(C₁–C₆)alkoxy substituted phenylamino, diphenylamino, mono- ordi(C₁–C₆)alkyl substituted diphenylamino, mono- or di(C₁–C₆)alkoxysubstituted diphenylamino, morpholino or piperidino; R₇₂ being chosenfrom hydrogen, —C(O)R₆₉, C₁–C₆ alkyl, C₁–C₃ alkoxy(C₁–C₆)alkyl,phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl, each of said aryl group substituents being independentlychosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (vii) the group T being thesame as described hereinbefore in (2)(d)(i); or (viii) R₇₄ and R₇₅together form an oxo group or a substituted or unsubstitutedspiro-carbocyclic ring containing 3 to 6 carbon atoms or a substitutedor unsubstituted spiro-heterocyclic group containing 1 or 2 oxygen atomsand 3 to 6 carbon atoms including the spirocarbon atom, saidspiro-carbocyclic ring and spiro-heterocyclic group being annellatedwith 0, 1 or 2 benzene rings, said substituents being hydrogen or C₁–C₆alkyl; (b) R₇₆ is independently chosen for each occurrence fromdi(C₁–C₆)alkylamino, dicyclohexylamino, diphenylamino, piperidyl,morpholinyl, pyridyl, a group T, described hereinbefore in (2)(d)(i); orgroup —C(O)W″, wherein each W″ is hydroxy, C₁–C₆ alkyl, C₁–C₆ alkoxy,phenyl, mono-substituted phenyl, amino, mono(C₁–C₆)alkylamino,morpholino, piperidino or pyrrolidyl; substituents being C₁–C₆ alkoxy;and q is the integer 0, 1, or 2; or when q is 2, and the R₇₆substituents are adjacent, each pair of substituents independently formsa substituted or unsubstituted fused carbocyclic or heterocyclic ringchosen from benzo, pyridino, pyrazino, pyrimidino, furano,dihydrofurano, 1,3-dioxolo, 1,4-dioxolo, 1,3-dioxino, 1,4-dioxino,thiopheno, benzofuro, benzothieno, indolo, or indeno, the substituentsof said fused carbocyclic or heterocyclic ring being chosen fromhalogen, C₁–C₆ alkyl, C₁–C₆ alkoxy, amino, mono- or di-substitutedamino, said amino substituents being chosen from C₁–C₆ alkyl, phenyl,benzyl or naphthyl; said first R₇₆ ring being fused to the o, p or qside and said second R₇₆ ring being fused to the g, h, or i side of theindenonaphthopyran; and (c) B and B′ are each independently chosen fromthe groups described hereinbefore in (2)(d); or (14) mixtures thereof.5. The photochromic article of claim 4 wherein photochromic material (c)is chosen from: (1) a photochromic material represented by graphicformula I wherein: (a) R₁ is chosen from C₁–C₈ alkyl, phen(C₁–C₄)alkyl,acrylyloxy(C₂–C₆)alkyl, methacrylyloxy(C₂–C₆)alkyl, carboxy(C₂–C₆)alkyl,tri(C₁–C₆)alkylsilyl, tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyl,di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silylor di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyloxy; (b) R₂ is chosen from C₁–C₅alkyl, C₁–C₅ alkoxy, C₁–C₈ alkoxycarbonyl, C₁–C₄ acyloxy, halo, C₁–C₄monohaloalkyl or C₁–C₄ polyhaloalkyl; said halo substituents beingchloro or fluoro, and q is 0, 1 or 2; (c) R₃ and R₄ are eachindependently chosen from C₁–C₅ alkyl, phenyl; or R₃ and R₄ takentogether form a group chosen from a cyclic ring of from 5 to 8 carbonatoms which includes the spiro carbon atom; (d) R₅ is chosen from —CH₂Qand —C(O)W, wherein Q is halogen, hydroxy, C₁–C₆ alkoxy,tri(C₁–C₆)alkylsilyl, tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyl,di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyl,di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyloxy, or the group, —OCH(R₈)Z; W is thegroup, —OCH(R₈)Z, morpholino or piperidino; Z is —COOR₈, R₈ is C₁–C₆alkyl; or W is —OR₉ or —N(R₁₀)R₁₁, wherein R₉ is chosen from C₁–C₆ alkylor phenyl; and R₁₀ and R₁₁ are each independently chosen from hydrogen,C₁–C₆ alkyl, or R₁₀ and R₁₁ together with the nitrogen atom form aheterocyclic ring chosen from morpholino or piperidino; and each of saidhalogen or halo groups in this part (d) being fluoro or chloro; (e) eachR₆ and R₇ is independently chosen for each occurrence from aryl,mono(C₁–C₆)alkoxyaryl, di(C₁–C₆)alkylamino, piperidino, morpholino,C₁–C₆ alkoxy, or fluoro; and q is independently chosen for eachoccurrence form the integer 0, 1, or 2, (2) a photochromic materialrepresented by graphic formula II wherein: (a) R₁₂ is hydrogen; (b) R₁₃is hydrogen or the group, —C(O)J, J being —OR₁₅ or —N(R₁₀)R₁₁, whereinR₁₅ is C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, or C₁–C₆ alkoxy(C₂–C₄)alkyl, R₁₀and R₁₁ are the same as described hereinbefore in (1)(d); (c) R₁₄ ishydrogen, C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, C₁–C₆ alkoxy(C₂–C₄)alkyl,C₅–C₇ cycloalkyl, or the group, —C(O)V; wherein V is C₁–C₆ alkyl, C₁–C₆alkoxy or C₁–C₆ alkylamino; and (d) B and B′ are each independentlychosen from: (i) an unsubstituted, mono-, di-, or tri-substituted phenylgroup; (ii) a mono-substituted heteroaromatic group chosen frombenzofuran-2-yl, benzothien-3-yl, dibenzofuranyl, or carbazoyl; each ofsaid phenyl and heteroaromatic substituents in (i) and (ii) beingindependently chosen from —C(O)U, wherein U being C₁–C₆ alkyl, C₁–C₆alkoxy, mono(C₁–C₆)alkylamino, di-(C₁–C₆)alkylamino, morpholino, orpiperidino; or amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino,piperidino, morpholino or fluoro; (iii) an unsubstituted ormono-substituted phenothiazinyl, said substituents being C₁–C₆ alkyl orC₁–C₆ alkoxy; (iv) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being —O—(CH₂)_(r)—, wherein rbeing chosen from the integer 3 or 6, said substituent being connectedto an aryl group which is a member of another photochromic material; (v)a group represented by one of the following graphic formulae:

 wherein A being independently chosen in each formula from methylene oroxygen and D being independently chosen in each formula from oxygen orsubstituted nitrogen, provided that when D is substituted nitrogen, A ismethylene; said nitrogen substituents being C₁–C₆ alkyl; each R₂₀ beingindependently chosen for each occurrence in each formula from C₁–C₆alkyl or C₁–C₆ alkoxy; R₁₈ and R₁₉ each being independently chosen ineach formula from hydrogen or C₁–C₆ alkyl; and q being chosen theinteger 0, 1 or 2; (vi) C₁–C₆ alkyl, C₃–C₆ cycloalkyl, or C₄–C₁₂bicycloalkyl; (vii) a group represented by the following graphicformula:

 wherein L being hydrogen and M being an unsubstituted, mono-, ordi-substituted phenyl; each of said group substituents beingindependently chosen from C₁–C₄ alkoxy or fluoro; or (viii) B and B′taken together form fluoren-9-ylidene, mono-, or di-substitutedfluoren-9-ylidene or a saturated C₇–C₁₂ spiro-bicyclic hydrocarbonrings; each of of said fluoren-9-ylidene substituents being fluoro; (3)a photochromic material represented by graphic formula III wherein: (a)R₂₁ is the group, —C(O)W or CH₂Q, described hereinbefore in (1)(d); (b)R₂₂ and each R₂₃ are independently chosen for each occurrence fromhydroxy, NH₂ or N(R)H; wherein R is C₁–C₃ alkyl or phenyl and n ischosen from the integers 0, 1 or 2; (c) B and B′ are each independentlychosen from the groups described hereinbefore in (2)(d); (4) aphotochromic material represented by graphic formula IV wherein: (a) R₅is chosen from the groups described hereinbefore in (1)(d); (b) R₂₄ andR₂₅ are each chosen from hydrogen or an amino group defined hereinafter,provided that R₂₄ and R₂₅ are not both hydrogen; said amino group being:(i) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each being independently chosen from C₁–C₈alkyl, aryl, or C₃–C₂₀ cycloalkyl; and said aryl group being phenyl ornaphthyl; (ii) a nitrogen containing ring represented by the followinggraphic formula:

 wherein each Y being independently chosen for each occurrence from—CH₂—, ; X being —Y—, —O—, —S—, or —N(R₂₆)—; R₂₆ being C₁–C₆ alkyl; saidaryl group being phenyl or naphthyl, m being chosen from the integer 1,2 or 3 and p being chosen from the integer 0, 1, 2 or 3; provided thatwhen p is 0, X is Y; or (iii) a group represented by one of thefollowing graphic formulae:

 wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen; R₂₇ being chosen independentlyfor each occurrence from C₁–C₆ alkyl, and q being chosen from theinteger 0, 1 or 2; (c) B and B′ are each independently chosen from thegroups described hereinbefore in (2)(d); (5) a photochromic materialrepresented by graphic formula V wherein: (a) R₃₁ is R₅ describedhereinbefore in (1)(d); (b) R₃₂ is hydrogen or C₁–C₆ alkyl; (c) each R₃₃is independently chosen for each occurrence from —N(R₁₀)R₁₁, which wasdescribed hereinbefore in (1)(d), C₁–C₆ alkyl, or —OR₃₄, wherein R₃₄ isC₁–C₆ alkyl, and q is the integer 0, 1, or 2; and (d) B and B′ are eachindependently chosen from the groups described hereinbefore in (2)(d);(6) a photochromic material represented by graphic formula VI wherein:(a) R₃₅ and R₃₆ are each independently chosen for each occurrence fromC₁–C₆ alkyl, C₁–C₆ alkoxy, fluoro, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, phenylamino, mono-or di-(C₁–C₆)alkyl substitutedphenylamino or mono- or di-(C₁–C₆)alkoxy substituted phenylamino, and qis the integer 0, 1 or 2; (b) R₅ is chosen from the group describedhereinbefore in (1)(d); and (c) B and B′ are each independently chosenfrom the groups described hereinbefore in (2)(d); (7) a photochromicmaterial represented by graphic formula VII wherein: (a) R₃₇ and R₃₈together form an oxo group or R₃₇ and R₃₈ each are independently chosenfor each occurrence from hydrogen, C₁–C₆ alkyl, C₃–C₇ cycloalkyl, phenylor methacryloxy(C₁–C₆)alkyl; (b) R₃₉ is chosen from C₁–C₆ alkyl, C₁–C₆alkoxy, fluoro, or morpholino, and q is the integer 0, 1 or 2; (c) I isoxygen or —N(R₄₀)—, wherein R₄₀ is C₁–C₆ alkyl, C₃–C₇ cycloalkyl orphenyl; (d) K is oxygen, —N(R₄₀)— or —C(R₄₁)(R₄₂)—, wherein R₄₁ and R₄₂are each hydrogen or C₁–C₆ alkyl; and (e) B and B′ are eachindependently chosen from the groups described hereinbefore in (2)(d);(8) a photochromic material represented by graphic formula VIII wherein:(a) R₄₃ and R₄₄ together form an oxo group or R₄₃ and R₄₄ are bothhydrogen, C₁–C₆ alkyl, C₃–C₇ cycloalkyl or phenyl; (b) R₄₅ is hydrogenor C₁–C₆ alkyl; (c) R₄₆ is hydrogen or C₁–C₆ alkyl, C₃–C₇ cycloalkyl;(d) each R₄₇ is C₁–C₆ alkyl, C₁–C₆ alkoxy or fluoro, and q is theinteger 0, 1 or 2; and (e) B and B′ are each independently chosen fromthe groups described hereinbefore in (2)(d); (9) a photochromic materialrepresented by graphic formulae IXA, IXB, IXC, IXD, IXE, IXF, IXG or IXHwherein: (a) R₄₃ and R₄₄ are the same groups described hereinbefore in(8)(a); (b) each R₄₇ and q are the same as described hereinbefore in(8)(d); and (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (2)(d); (10) a photochromic materialrepresented by graphic formulae XA or XB wherein: (a) A′ is chosen from:(i) an unsubstituted, mono- or di-substituted heterocyclic ring; or (ii)an unsubstituted, mono- or di-substituted indeno group, each of saidheterocyclic ring and indeno group substituents being C₁–C₄ alkyl, C₁–C₃alkoxy, —N(R₁₀)R₁₁, which was described hereinbefore in (1)(d), benzo,mono- or di-substituted benzo fused to the indeno moiety, said benzosubstituents being C₁–C₃ alkyl, C₁–C₃ alkoxy or —N(R₁₀)R₁₁; (b) R₄₈ ischosen from: (i) —C(O)W′, W′ being —OR₉ or —N(R₁₀)R₁₁, which groups weredescribed hereinbefore in (1)(d); or (ii) —C(R₅₁)₂X′, wherein X′ is —CN,halogen, hydroxy, benzoyloxy, C₁–C₄ alkoxy, C₂–C₄ acyloxy, amino, C₁–C₄mono-alkylamino, C₁–C₄ dialkylamino, morpholino, piperidino, 1-indolinylor pyrrolidyl, and R₅₁ is hydrogen, C₁–C₄ alkyl, phenyl or naphthyl; (c)R₄₉ is hydrogen, C₁–C₄ alkyl, the mono- or di-substituted aryl groupsphenyl or naphthyl, said aryl substituents being C₁–C₄ alkyl or C₁–C₄alkoxy, chloro or fluoro; (d) each R₅₀ is fluoro, C₁–C₄ alkyl, C₁–C₄alkoxy, phenyl, naphthyl, phenoxy, naphthoxy, or the group, —N(R₁₀)R₁₁,described hereinbefore in (1)(d), and q is selected from the integers 0,1 or 2 for the naphthopyran represented by graphic formula XA or p isselected from the integers 0, 1, 2 or 3 for the naphthopyran representedby graphic formula XB; and (e) B and B′ are each independently chosenfrom the groups described hereinbefore in (2)(d); (11) a photochromicmaterial represented by graphic formulae XIA or XIB wherein: (a) A″ isan unsubstituted, mono-substituted or di-substituted heterocyclic ringchosen from furo, thieno, benzothieno, benzofurano or indolo, the 2,3 or3,2 positions of said heterocyclic ring being fused to the p side ofsaid indenonaphthopyran, said heterocyclic ring substituents being C₁–C₆alkyl; (b) R₅₂ and R₅₃ together form an oxo group, a spiro heterocyclicgroup having 2 oxygen atoms and from 3 to 6 carbon atoms including thespirocarbon atom, or R₅₂ and R₅₃ are each hydrogen, hydroxy, C₁–C₆alkyl, C₃–C₇ cycloalkyl, phenyl or the group, —C(O)W″, wherein each W″is C₁–C₆ alkoxy, mono(C₁–C₆)alkylamino or di(C₁–C₆)alkylamino, or R₅₂and R₅₃ are each the group, —N(R₁₀)R₁₁, described hereinbefore in(1)(d), or —OR₅₄, wherein each R₅₄ is C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl,the group, —CH(R₅₅)X″, wherein each R₅₅ is hydrogen or C₁–C₃ alkyl, eachX″ is —COOR₅₅, or each R₅₄ is the group, —C(O)Y′, wherein each Y′ isC₁–C₆ alkyl; (c) each R₄₇ and q are the same as described hereinbeforein (8)(d); and (d) B and B′ are each independently chosen from thegroups described hereinbefore in (2)(d); (12) a photochromic materialrepresented by graphic formulae XIIA or XIIB wherein: (a) A″ is the sameas the groups described hereinbefore in (11)(a); (b) R₅₆ is hydrogen orhydroxy and R₅₇ is the group, —CH(V′)₂, wherein V′ is —COOR₅₈, and eachR₅₈ is C₁–C₆ alkyl or phenyl(C₁–C₃)alkyl; or R₅₇ is the group,—CH(R₅₉)Y″, wherein R₅₉ is hydrogen and Y″ is —COOR₅₈, or —CH₂OR₆₀wherein R₅₉ is C₁–C₆ alkyl or di(C₁–C₆)alkylamino; and R₆₀ is C₁–C₆alkyl; or (c) R₅₆ and R₅₇ together form the group, ═C(R₅₉)W′″, whereinW′″ is —COOR₅₈; (d) each R₄₇ and q are the same as describedhereinbefore in (8)(d); and (e) B and B′ are each independently chosenfrom the groups described hereinbefore in (2)(d); (13) a photochromicmaterial represented by graphic formula XIV wherein: (a) R₇₄ and R₇₅ areeach independently chosen from: (i) hydrogen, hydroxy, amino, mono- ordi-substituted amino, C₁–C₁₂ alkyl, C₃–C₁₂ alkylidene, C₂–C₁₂alkylidyne, vinyl, C₃–C₇ cycloalkyl, C₁–C₆ alkoxyalkyl, allyl, benzyl,mono-substituted benzyl, chloro, fluoro or —C(O)W″, wherein W″ being thesame group described hereinbefore in (11)(b); said amino substituents in(a)(i) being C₁–C₆ alkyl, phenyl, benzyl or naphthyl; each of saidbenzyl substituents being C₁–C₆ alkyl or C₁–C₆ alkoxy; (ii) anunsubstituted, mono- di- or tri-substituted group chosen from phenyl,naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl,thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl orindolyl; each of said group substituents in (a)(ii) being chosenindependently for each occurrence from chloro, fluoro, C₁–C₆ alkyl orC₁–C₆ alkoxy; (iii) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being as described hereinbeforein (2)(d)(v); (iv) —OR_(67′), R_(67′) being chosen from C₁–C₆ alkyl,C₁–C₆ acyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl,C₁–C₆ alkoxyl(C₂–C₄)alkyl, C₃–C₇ cycloalkyl, mono(C₁–C₄)alkylsubstituted C₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl,allyl, triarylsilyl, triarysilyloxy, tri(C₁–C₆)alkylsilyl,tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyl,di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆alkyl)silyl,di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyloxy, benzoyl, mono-substituted benzoyl,naphthoyl or mono-substituted naphthoyl; each of said benzoyl andnaphthoyl substituents being independently chosen from C₁–C₆ alkyl orC₁–C₆ alkoxy; or R_(67′) being —CH(R₆₈)Q″, wherein R₆₈ being chosen fromhydrogen or C₁–C₃ alkyl and Q″ being chosen from —CN, —CF₃, or COOR₆₈;or R_(67 ′) being —C(O)V″, wherein V″ being chosen from hydrogen, C₁–C₆alkoxy, phenoxy, mono- or di-(C₁–C₆)alkyl substituted phenoxy, mono- ordi-(C₁–C₆)alkoxy substituted phenoxy, an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, amino,mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, phenylamino, mono- ordi-(C₁–C₆)alkyl substituted phenylamino, or mono- or di-(C₁–C₆)alkoxysubstituted phenylamino; each of said aryl group substituents beingindependently chosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (v) —CH(Q′″)₂,Q′″ being chosen from —CN or —COOR₆₉ and R₆₉ being chosen from hydrogen,C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl; each of said aryl group substituents being independentlychosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (vi) —CH(R₇₀)G″, R₇₀ beingchosen from hydrogen, C₁–C₆ alkyl or an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, and G″ being chosen from—COOR₆₉, —COR₇₁ or —CH₂OR₇₂, wherein R₇₁ being chosen from hydrogen,C₁–C₆ alkyl, an unsubstituted, mono- or di-substituted aryl group,phenyl or naphthyl, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino,phenylamino, mono- or di-(C₁–C₆)alkyl substituted phenylamino, mono- ordi-(C₁–C₆)alkoxy substituted phenylamino, diphenylamino, mono- ordi(C₁–C₆)alkyl substituted diphenylamino, mono- or di(C₁–C₆)alkoxysubstituted diphenylamino, morpholino or piperidino; R₇₂ being chosenfrom hydrogen, —C(O)R₆₉, C₁–C₆ alkyl, C₁–C₃ alkoxy(C₁–C₆)alkyl,phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl, each of said aryl group substituents being independentlychosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (vii) the group T being thesame as described hereinbefore in (2)(d)(i); or (viii) R₇₄ and R₇₅together form an oxo group or a substituted or unsubstitutedspiro-carbocyclic ring containing 3 to 6 carbon atoms or a substitutedor unsubstituted spiro-heterocyclic group containing 1 or 2 oxygen atomsand 3 to 6 carbon atoms including the spirocarbon atom, saidspiro-carbocyclic ring and spiro-heterocyclic group being annellatedwith 0, 1 or 2 benzene rings, said substituents being hydrogen or C₁–C₆alkyl; (b) each R₇₆ is independently chosen from di(C₁–C₆)alkylamino,dicyclohexylamino, diphenylamino, piperidyl, morpholinyl, pyridyl,halogen, or group —C(O)W″, wherein W″ being the same group describedhereinbefore in (11)(b) and q is the integer 0, 1, or 2; or when q is 2,and the R₇₆ substituents are adjacent, each pair of substituentsindependently forms a substituted or unsubstituted fused carbocyclic orheterocyclic ring chosen from benzo, dihydrofurano, 1,4-dioxolo,1,3-dioxino, or benzofuro, the substituents of said fused carbocyclic orheterocyclic ring being chosen from the group consisting of C₁–C₆ alkylor C₁–C₆ alkoxy; (c) B and B′ are each independently chosen from thegroups described hereinbefore in (2)(d); or (14) mixtures thereof. 6.The photochromic article of claim 5 wherein photochromic material (c) ischosen from: (1) a photochromic material represented by graphic formulaI chosen from: (a)1,3,3-trimethyl-spiro[indoline-2,5′-3H-fluorantheno[3,2-b][1,4]oxazine];(b) 1,3,3,4,5 (or1,3,3,5,6)-pentamethyl-spiro[indoline-2,5′-3H-fluorantheno[3,2-b][1,4]oxazine];(c) 1-propyl-3,3,4,5 (or3,3,5,6)-tetramethyl-spiro[indoline-2,5′-3H-fluorantheno[3,2-b][1,4]oxazine];or (d)1-methoxyethyl-3,3-dimethyl-spiro[indoline-2,5′-3H-fluorantheno[3,2-b][1,4]oxazine];(2) a photochromic material represented by graphic formula II chosenfrom: (a) 3,3-diphenyl-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;(b)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;(c)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(d)3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbomethoxy-3H-naphtho{2,1-b]pyran;(e) 3,3-diphenyl-8-methoxy-9-carbophenoxy-3H-naphtho[2,1-b]pyran; (f)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-methoxy-9-carbophenoxy-3H-naphtho[2,1-b]pyran;(g)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(h)3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(i) 3,3-diphenyl-7-methyl-8-methoxy-3H-naphtho[2,1-b]pyran; (j)3-(2-methoxy,4-acryloxyphenyl)-3-(4-methacryloxyphenyl)-8-benzyloxy-9-(carbo-1-indolinyl-3H-naphtho[2,1-b]pyran;(k)3-(2,4,6-trifluorophenyl)-3-(2,4,6-trimethoxy-1-naphthyl)-8-acetyl-9-carboniloyl-3H-naphtho[2,1-b]pyran;(l)3-(2-fluorophenyl)-3-(3-methoxy-2-thienyl)-7-h-pentyl-8-benzoyloxy-3H-naphtho[2,1-b]pyran;(m)3,3-spiroadamantylene-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(n)3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(o)3-(4-methoxyphenyl)-3-(2-phenyl-1-methylvinyl)-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(p)3-(4-methoxyphenyl)-3-(9-ethylcarbozol-2-yl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(q)3,3-spirofluoren-9-ylidene-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;or (r) 3,3-diphenyl-8-morpholino-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(3) a photochromic material represented by graphic formula III chosenfrom: (a)2,2-di(4-methoxyphenyl)-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;(b)2,2-di(4-methoxyphenyl)-5-methoxycarbonyl-6-amino-2H-naphtho[1,2-b]pyran;(c)2,2-di(4-methoxyphenyl)-5-methoxycarbonyl-6-propylamino-2H-naphtho[1,2-b]pyran;(d)2-(4-methoxyphenyl)-2-t-butyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;(e)2-(4-methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-amino-2H-naphtho[1,2-b]pyran;(f)2,2-(4-methylphenyl)-5-methoxycarbonyl-6-methylamino-2H-naphtho[1,2-b]pyran;(g) 2,2-diphenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran; (h)2,2-di(4-methoxyphenyl)-5-methoxycarbonyl-6-phenylamino-2H-naphtho[1,2-b]pyran;(i)2,2-di(4-methoxyphenyl)-5-methoxycarbonyl-6-hydroxy,9-methoxy-2H-naphtho[1,2-b]pyran;(j) 2,2-diphenyl-5-methoxycarbonyl-6-phenylamino-2H-naphtho[1,2-b]pyran;(k)2,2di-(3-trifluoromethylphenyl)-5-methoxycarbonyl,6-hydroxy-2H-naphtho[1,2-b]pyran;(l)2-(4-methoxyphenyl)-2-(2-methyl,2,3-dihydrobenzofur-5-yl),5-methoxycarbonyl-6-amino-2H-naphtho[1,2-b]pyran;or (m)2,2′-spiroadamantylene-5-methoxycarbonyl-6-methoxy-2H-naphtho[1,2-b]pyran;(4) a photochromic material represented by graphic formula IV chosenfrom: (a)2-phenyl-2-(4-morpholinophenyl)-5-carbomethoxy-9-dimethylamino-2H-naphtho[1,2-b]pyran;(b)2,2-di(4-methoxyphenyl)-5-methoxymethyl-9-morpholino-2H-naphtho[1,2-b]pyran;or (c)2-(4-methoxyphenyl)-2-(4-piperidinophenyl)-5-carbomethoxy-9-dimethylamino-2H-naphtho[1,2-b]pyran.(5) a photochromic material represented by graphic formula V chosenfrom: (a)3,3-diphenyl-12-methoxycarbonyl-11-methyl-3H-phenanthro[1,2-b]pyran; (b)2,2-diphenyl-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran; (c)2-(4-methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran;(d)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-6-methoxy-12-methoxycarbonyl-3H-phenanthro[1,2-b]pyran;(e)spiro[3H-6-methoxy-12-methoxycarbonyl-phenanthro[1,2-b]pyran-3-9′-fluorene];(f)2,2-di(4-methoxyphenyl)-10-methoxy-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran;(g)3-(2,3-dihydrobenzofur-5-yl)-3-(4-methoxyphenyl)-6-methoxy-12-methoxycarbonyl-11-methyl-3H-phenanthro[1,2-b]pyran;(h)3,3-diphenyl-6-methoxy-12-methoxycarbonyl-11-phenyl-3H-phenanthro[1,2-b]pyran;(i)3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-6-methoxy-12-methoxycarbonyl-11-phenyl-3H-phenanthro[1,2-b]pyran;(j)3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-6-methoxy-12-hydroxymethyl-11-phenyl-3H-phenanthro[1,2-b]pyran;or (k)2,2-diphenyl-5-N,N-dimethylaminocarbonyl-2H-phenanthro[4,3-b]pyran; (6)a photochromic material represented by graphic formula VI chosen from:(a)5,5-bis(4-methoxyphenyl)-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran;(b)5-(4-methoxyphenyl)-5-(4-morpholinophenyl)-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran;(c) 5,5-diphenyl-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran; (d)5,5-bis(4-methoxyphenyl)-8-methylol-5H-fluorantheno[3,2-b]pyran; or (e)5,5-bis(4-methoxyphenyl)-2-methoxy-8-methoxycarbonyl-5H-fluorantheno[3,2-b]pyran;(7) a photochromic material represented by graphic formula VII chosenfrom: (a)7,7-diphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran; (b)7,7-di(4-methoxyphenyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(c)7-(4-methoxyphenyl)-7-phenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(d)7,7-diphenyl-2-ethyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(e)7,7-diphenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(f)7,7-diphenyl-2-(2-methylpropyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[12-b]pyran;(g)2,7,7-triphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(h)7,7-diphenyl-2-(l-phenylethyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(i)3-methyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(j)3-(2-ethoxycarbonylethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(k)3-hexyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(l)3-(2-methacryloyloxyethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran; (m)2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-pyrimidino[5′,4′:3,4]naphtho[1,2-b]pyran;(n)2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-[1,3]oxazino[5′,4′:3,4]naphtho[1,2-b]pyran;(o)7,7-diphenyl-1,2,4,7-tetrahydro-2,2-dimethylpyrano[3′,4′:3,4]naphtho[1,2-b]pyran;(p)7-phenyl-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(q)7-(2-fluorophenyl)-7-(3-methyl-4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(r)7-(4-methoxyphenyl)-7-(2,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(s)7-(4-morpholino-2-fluorophenyl)-7-(4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(t)7-(2-fluoro-4-methoxyphenyl)-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;or (u)7-(4-morpholino-2-fluorophenyl)-7-(3,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(8) the photochromic material: (a)2-(4-methoxyphenyl)-2-(2,4-dimethoxy-phenyl)-7-diphenylmethyl-10-methyl-5-oxo-2H-5H-pyrano[3′,4′:3,4]naphtho[1,2-b]pyran;(9) a photochromic material represented by graphic formula IXA, IXB, IXCor IXD chosen from: (a)2,2-bis(4-methoxyphenyl)-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(b)6,6-bis(4-methoxyphenyl)-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(c)6,6-bis(4-methoxyphenyl)-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(d)2-(4-methoxyphenyl)-2-(4-morpholinophenyl)-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran; (e)6-(4-methoxyphenyl)-6-(4-morpholinophenyl)-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(f)10,10-dimethyl-6-(4-methoxyphenyl)-6-(4-morpholinophenyl)-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(g)2-(4-morpholinophenyl)-2-phenyl-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(h)6-(4-morpholinophenyl)-6-phenyl-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(i)2,2-bis(4-methoxyphenyl)-12,13-dimethoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(j) 6,6-bis(4-methoxyphenyl)-1 2,1 3-dimethoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho (1,2-b)pyran; (k)6-(4-methoxyphenyl)-6-phenyl-12,13-dimethoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(l)2-(4-methoxyphenyl)-2-phenyl-12,13-dimethoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(m)6-(4-methoxyphenyl)-6-phenyl-12,13-dimethoxy-10,10-dimethyl-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(n)2,2-bis(4-methoxphenyl)-12-methoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(o)6,6-bis(4-methoxyphenyl)-12-methoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(p)6,6-diphenyl-9-oxo-6,9-dihydro[1]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;or (q)3,3-diphenyl-8-oxo-3,8-dihydro[2]benzopyrano[3′,4′:5,6]naphtho(2,1-b)pyran;(10) a photochromic material represented by graphic formula XA or XBchosen from: (a)2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[1,2-b]pyran;(b)2-(4-methoxyphenyl)-2-(4-propoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[1,2-b]pyran;(c)2,2′-spiroadamantylene-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[1,2-b]pyran;(d)3,3-bis(4-methoxyphenyl)-10-methoxy-3H-naphtho[2″,1″:4′,5′]furo[2′,3′:3,4]naphtho[1,2-b]pyran;(e)3,3-bis(4-methoxyphenyl)-3H-naphtho[1″,2″:4′,5′]furo[3′,2′:3,4]naphtho[1,2-b]pyran;(f)3,3′-spiroadamantylene-3H-naphtho[1″,2″:4′,5′]furo[3′,2′:3,4]naphtho[1,2-b]pyran;(g)2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-indeno[3′,2′:7:8]naphtho[1,2-b]pyran;(h)3,3-di(4-methoxyphenyl)-6,11-dimethoxy-13-butyl-13-ethoxy-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;or (i)3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(11) a photochromic material represented by graphic formula XIA or XIBchosen from: (a)3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(b)3,3-di(4-methoxyphenyl)-16-hydroxy-[16H]-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;or (c)3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;(12) a photochromic material represented by graphic formula XIIA or XIIBchosen from: (a)3,3-di(4-methoxyphenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(b)3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(c)3-phenyl-3-(4-methoxyphenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;or (d)3-phenyl-3-(4-morpholinophenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;(13) a photochromic material represented by graphic formula XIV chosenfrom: (a) 3,3,9-triphenyl-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(b)3,3-di(4-methoxyphenyl)-9-phenyl-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(c)3-(4-methoxyphenyl)-3,9-diphenyl-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(d)3-(4-morpholinophenyl)-3,9-diphenyl-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(e)3,3-di(4-methoxyphenyl)-9-(3-methoxyphenyl)-11-methoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(f)3-(4-methoxyphenyl)-3-phenyl-9-(3-methoxyphenyl)-11-methoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(g)3-(4-methoxyphenyl)-3-phenyl-9-methyl-11-methoxy-9-(3-methoxyphenyl)-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(h)3,3-di(4-methoxyphenyl)-9-methyl-11-methoxy-9-(3-methoxyphenyl)-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(i)3,3-di(4-methoxyphenyl)-9-methyl-11-methoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(j)3,3-di(4-methoxyphenyl)-9,9-dimethyl-11-methoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(k)3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-11-methoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(l)3,3-di(4-methoxyphenyl)-9,9-dimethyl-7,11-dimethoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(m)3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-7,11-dimethoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(n)3-(4-morpholinophenyl)-3-phenyl-9,9-dimethyl-7,11-dimethoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(o)3,3-di(4-methoxyphenyl)-9-methyl-11,13-dimethoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(p)3-(4-methoxyphenyl)-3-phenyl-9-methyl-11,13-dimethoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(q)3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;or (r)3,3-di(4-methoxyphenyl-9,9-dimethyl-11-fluoro-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;or (14) mixtures thereof.
 7. The photochromic article of claim 6 whereinphotochromic material (c) is chosen from: (a)7,7-diphenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(b)7-phenyl-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(c)7-(2-fluorophenyl)-7-(3-methyl-4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(d)3-(4-methoxyphenyl)-3-phenyl-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(e)2-(4-methoxyphenyl)-2-(2,4-dimethoxyphenyl)-7-diphenylmethyl-10-methyl-5-oxo-2H-5H-pyrano[3′,4′:3,4]naphtho[1,2-b]pyran;(f)7-(4-methoxyphenyl)-7-(2,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(g)7-(4-morpholino-2-fluorophenyl)-7-(4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(h)7-(2-fluoro-4-methoxyphenyl)-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(i)7-(4-morpholino-2-fluorophenyl)-7-(3,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(j)3,3-di(4-methoxyphenyl)-6,11-dimethoxy-13-butyl-13-ethoxy-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran; (k)3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;or (l) mixtures thereof.
 8. The photochromic article of claim 1 furthercomprising at least one fixed tint dye.
 9. The photochromic article ofclaim 1 wherein said photochromic article is adapted to exhibit aneutral activated color.
 10. The photochromic article of claim 1 whereinthe photochromic article is adapted to retain at least 20 percent ofsaid ΔOD.
 11. The photochromic article of claim 1 further comprising anat least partial coating of an at least partially abrasion resistantcoating applied to at least one surface of the substrate.
 12. Thephotochromic article of claim 11 further comprising an at least partialcoating of an at least partially antireflective coating applied to theat least partial coating of an at least partially abrasion resistantcoating.
 13. The photochromic article of claim 1 wherein the substratecomprises at least one photochromic material (b).
 14. The photochromicarticle of claim 13 wherein the substrate further comprises at least onephotochromic material (c) that is different from photochromic material(b).
 15. The photochromic article of claim 1 further comprising an atleast partial coating of an at least partially cured polymeric coatingapplied to at least one surface of the substrate.
 16. The photochromicarticle of claim 15 wherein the at least partially cured polymericcoating comprises photochromic material (b).
 17. The photochromicarticle of claim 16 wherein the at least partially cured polymericcoating further comprises at least one other photochromic material (c)that is different from photochromic material (b).
 18. The photochromicarticle of claim 15 wherein the at least partially cured polymericcoating is a polymeric coating of thermoplastic or thermosettingmaterials.
 19. The photochromic article of claim 18 wherein the at leastpartially cured polymeric coating is a polymeric coating ofthermosetting materials chosen from polyurethanes, aminoplast resins,poly(meth)acrylates, polyanhydrides, polyacrylamides, epoxy resins orpolysilanes.
 20. The photochromic article of claim 15 further comprisingan at least partial coating of primer interposed between the at leastpartially cured polymeric coating and the substrate.
 21. Thephotochromic article of claim 20 further comprising an at least partialcoating of an at least partially abrasion resistant coating applied tothe surface of the at least partially cured polymeric coating.
 22. Thephotochromic article of claim 21 further comprising an at least partialcoating of an at least partially antireflective coating applied to theat least partial coating of an at least partially abrasion resistantcoating applied to the surface of the at least partially cured polymericcoating.
 23. The photochromic article of claim 1 wherein the substrateis chosen from paper, glass, ceramic, wood, masonry, textile, metal ororganic polymeric material.
 24. The photochromic article of claim 23wherein the substrate is organic polymeric material and said organicpolymeric material is chosen from poly(C₁–C₁₂ alkyl methacrylates),poly(oxyalkylene dimethacrylates), poly(alkoxylated phenolmethacrylates), cellulose acetate, cellulose triacetate, celluloseacetate propionate, cellulose acetate butyrate, poly(vinyl acetate),poly(vinyl alcohol), poly(vinyl chloride), poly(vinylidene chloride),thermoplastic polycarbonates, polyesters, polyurethanes, poly(ethyleneterephthalate), polystyrene, poly(alpha methylstyrene),copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile),polyvinylbutyral or is polymerized from monomers chosen from bis(allylcarbonate) monomers, polyfunctional acrylate monomers, polyfunctionalmethacrylate monomers, diethylene glycol dimethacrylate monomers,diisopropenyl benzene monomers, ethoxylated bisphenol A dimethacrylatemonomers, ethylene glycol bismethacrylate monomers, poly(ethyleneglycol) bismethacrylate monomers, ethoxylated phenol bis methacrylatemonomers, alkoxylated polyhydric alcohol polyacrylate monomers, styrenemonomers, urethane acrylate monomers, glycidyl acrylate monomers,glycidyl methacrylate monomers, diallylidene pentaerythritol monomers ormixtures thereof.
 25. The photochromic article of claim 24 wherein thesubstrate is an organic polymeric material and said organic polymericmaterial is an optical element.
 26. The photochromic article of claim 25wherein the substrate is an optical element and said optical element isan ophthalmic lens.
 27. The photochromic article of claim 1 furthercomprising a superstrate connected to at least a portion of thesubstrate, said superstrate comprising at least one organic polymericmaterial.
 28. The photochromic article of claim 27 wherein saidsuperstrate comprises photochromic material (b).
 29. The photochromicarticle of claim 28 wherein said superstrate further comprises at leastone other photochromic material (c) that is different from photochromicmaterial (b).
 30. The photochromic article of claim 27 wherein thesuperstrate is adheringly bonded to at least a portion of the substrate.31. The photochromic article of claim 27 wherein the superstrate is anorganic polymeric material chosen from thermosetting or thermoplasticmaterials.
 32. The photochromic article of claim 31 wherein thesuperstrate is a thermoplastic material and is polyurethane.
 33. Thephotochromic article of claim 27 further comprising an at leastpartially abrasion resistant film superposed on at least a portion ofthe superstrate.
 34. The photochromic article of claim 33 wherein the atleast partially abrasion resistant film is an organic polymeric materialchosen from thermoplastic and thermosetting materials.
 35. Thephotochromic article of claim 34 wherein the at least partially abrasionresistant film is a thermoplastic material and is polycarbonate.
 36. Thephotochromic article of claim 33 further comprising an at least partialcoating of an at least partially antireflective coating applied to theat least partially abrasion resistant film superposed on at least aportion of the superstrate.
 37. The photochromic article of claim 1wherein said photochromic article is substantially free of ultravioletradiation absorbing materials adapted to substantially inhibit theactivation of said photochromic material by radiation below 380nanometers.
 38. A photochromic article comprising: a) a substrate; andb) a photochromic amount of at least one organic photochromic materialb) adapted to change from an unactivated form to an activated form byradiation substantially in a wavelength range from 380 to 410 nanometerswhen measured over a range of from 380 to 700 nanometers, saidphotochromic article being adapted to exhibit an unactivated stateluminous transmittance of greater than 70 percent at 23° C., anactivated state luminous transmittance at saturation less than 30percent when activated at 23° C. by simulated sunlight from a xenon arclamp set at 6.7 Watts/meter² UVA and 50,000 lumens/meter², and anactivated state luminous transmittance at saturation less than 60percent when activated at 28° C. by simulated sunlight from a xenon arclamp through an UV blocking transparency rendering an irradianceintegrated between 380 and 420 nanometers of 0.75 Watts/meter² and 1,700lumens/meter², wherein said photochromic material (b) is represented bygraphic formula XIII

 wherein, (aa) R₆₁ is represented by: (i) —SR₆₇, R₆₇ being chosen fromC₁–C₆ alkyl, aryl, mono- or di-substituted aryl, said aryl group beingphenyl or naphthyl and each of said aryl substituents being chosenindependently from C₁–C₆ alkyl, C₁–C₆ alkoxy or halogen; or (ii) anamino group chosen from: (1) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each beingindependently chosen from hydrogen, C₁–C₈ alkyl, aryl, furanyl,benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl,benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl,fluorenyl, C₁–C₈ alkylaryl, C₃–C₂₀ cycloalkyl, C₄–C₂₀ bicycloalkyl,C₅–C₂₀ tricycloalkyl or C₁–C₂₀ alkoxyalkyl and said aryl group beingphenyl or naphthyl; (2) a nitrogen containing ring represented by thefollowing graphic formula:

 wherein each Y being independently chosen for each occurrence from—CH₂—, —CH(R₂₆)—, —C(R₂₆)(R₂₆)—, —CH(aryl)-, —C(aryl)₂— or—C(R₂₆)(aryl)-; X being —Y—, —O—, —S—, —S(O)—, —S(O₂)—, —NH—, —N(R₂₆)—or —N(aryl)-; R₂₆ being C₁–C₆ alkyl; said aryl group being phenyl ornaphthyl, m being chosen from the integer 1, 2 or 3 and p being chosenfrom the integer 0, 1, 2 or 3; provided that when p is 0, X is Y; (3) agroup represented by one of the following graphic formulae:

 wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen, C₁–C₅ alkyl, phenyl ornaphthyl; or the groups R₂₈ and R₂₉ together form a ring of 5 to 8carbon atoms; R₂₇ being chosen independently for each occurrence fromC₁–C₆ alkyl, C₁–C₆ alkoxy, fluoro or chloro and q being chosen from theinteger 0, 1 or 2; (4) unsubstituted, mono- or di-substituted C₄–C₁₈spirobicyclic amine; and (5) unsubstituted, mono- or di-substitutedC₄–C₁₈ spirotricyclic amine; said substituents for (4) and (5) beingindependently chosen for each occurrence from aryl, C₁–C₆ alkyl, C₁₋₆alkoxy or phenyl(C₁–C₆)alkyl; (bb) R₆₁′ is independently chosen for eachoccurrence from C₁–C₆ alkyl or C₁–C₆ alkoxy and q being chosen from theinteger 0, 1 or 2; (cc) R₆₂ and R₆₃ are each independently chosen from:(i) hydrogen, hydroxy, amino, mono- or di-substituted amino, C₁–C₁₂alkyl, C₃–C₁₂ alkylidene, C₂–C₁₂ alkylidyne, vinyl, C₃–C₇ cycloalkyl,C₁–C₆ alkoxyalkyl, allyl, benzyl, mono-substituted benzyl, chloro,fluoro or —C(O)W″, wherein W″ being hydroxy, C₁–C₆ alkyl, C₁–C₆ alkoxy,phenyl, mono-substituted phenyl, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, morpholino, piperidino or pyrrolidyl; said aminosubstituents in (cc)(i) being C₁–C₆ alkyl, phenyl, benzyl or naphthyl;each of said benzyl substituents being C₁–C₆ alkyl or C₁–C₆ alkoxy; (ii)an unsubstituted, mono- di- or tri-substituted group chosen from phenyl,naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl,thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, orindolyl; each of said group substituents in (cc)(ii) being chosenindependently for each occurrence from chloro, fluoro, C₁–C₆ alkyl orC₁–C₆ alkoxy; (iii) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being —(CH₂)_(r)— or—O—(CH₂)_(r)—, wherein r being chosen from the integer 1, 2, 3, 4, 5 or6, said substituent being connected to an aryl group which is a memberof another photochromic material; (iv) —OR_(67′), R_(67′) being chosenfrom C₁–C₆ alkyl, C₁–C₆ acyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkylsubstituted phenyl(C₁–C₃)alkyl, mono(C₁–C ₆)alkoxy substitutedphenyl(C₁–C₃)alkyl, C₁–C₆ alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl, mono(C₁–C₄)alkyl substituted C₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, allyl, triarylsilyl, triarylsilyloxy, tri(C₁–C₆)alkylsilyl,tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyl,di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyloxy, di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyl,di(C₁–C₆)alkoxy(C₁–C₆ alkyl)silyloxy, benzoyl, mono-substituted benzoyl,naphthoyl or mono-substituted naphthoyl; each of said benzoyl andnaphthoyl substituents being independently chosen from C₁–C₆ alkyl orC₁–C₆ alkoxy; or R_(67′) being —CH(R₆₈)Q″, wherein R₆₈ being chosen fromhydrogen or C₁–C₃ alkyl and Q″ being chosen from —CN, —CF₃, or COOR₆₈;R_(67′) being —C(O)V″, wherein V″ being chosen from hydrogen, C₁–C₆alkoxy, phenoxy, mono- or di-(C₁–C₆)alkyl substituted phenoxy, mono- ordi-(C₁–C₆)alkoxy substituted phenoxy, an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, amino,mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, phenylamino, mono- ordi-(C₁–C₆)alkyl substituted phenylamino, or mono- or di- C₁–C₆ alkoxysubstituted phenylamino; each of said aryl group substituents beingindependently chosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (v) CH(Q′″)₂, Q′″being chosen from —CN or COOR₆₉ and R₆₉ being chosen from hydrogen,C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl; each of said aryl group substituents being independentlychosen from C₁–C₆ alkyl or C₁–C₆ alkoxy: (vi) —CH(R₇₀)G″, R₇₀ beingchosen from hydrogen, C₁–C₆ alkyl or an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, and G″ being chosen from—COOR₆₉, —COR₇₁ or —CH₂OR₇₂, wherein R₇₁ being chosen from hydrogen,C₁–C₆ alkyl, an unsubstituted, mono- or di-substituted aryl group,phenyl or naphthyl, amino, mono (C₁–C₆)alkylamino, di(C₁–C₆)alkylamino,phenylamino, mono- or di-(C₁–C₆)alkyl substituted phenylamino, mono- ordi-(C₁–C₆)alkoxy substituted phenylamino, diphenylamino, mono- ordi(C₁–C₆)alkyl substituted diphenylamino, mono- or di(C_(1–C) ₆)alkoxysubstituted diphenylamino, morpholino or piperidino; R₇₂ being chosenfrom hydrogen, —C(O)R₆₉, C₁–C₆ alkyl, C₁–C₃ alkoxy(C₁–C₆)alkyl,phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl, each of said aryl group substituents being independentlychosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (vii) the group T wherein thegroup T is represented by the formula:-G[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′—[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′ wherein -G being chosen from—C(O)— or —CH₂—, G′ being chosen from C₁–C₃ alkoxy or a polymerizablegroup, x, y and z each being independently chosen from a number between0 and 50, and the sum of x, y and z being between 2 and 50; or (viii)R₆₂ and R₆₃ together form an oxo group or a substituted or unsubstitutedspiro-carbocyclic ring containing 3 to 6 carbon atoms or a substitutedor unsubstituted spiro-heterocyclic group containing 1 or 2 oxygen atomsand 3 to 6 carbon atoms including the spirocarbon atom, saidspiro-carbocyclic ring and spiro-heterocyclic group being annellatedwith 0, 1 or 2 benzene rings, said substituents being hydrogen or C₁–C₆alkyl; (dd) R₆₄ is hydrogen or C₁–C₆ alkyl; (ee) R₆₅ is hydrogen orC₁–C₆ alkyl; (ff) R₆₆ is chosen from hydrogen, C₁–C₆ alkyl or the groupR_(a), said R_(a) chosen from: (i) —OR₇₃, R₇₃ being chosen fromphenyl(C₁–C₃)alkyl, C₁–C₆ alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl,C₁–C₆ alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl, mono(C₁–C₄)alkyl substitutedC₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl, allyl or—CH(R₆₈)Q″ described in (cc)(i); or (ii) an amino group being the samedescribed hereinbefore in (aa)(ii);

 and (gg) B and B′ are each independently chosen from (i)mono-T-substituted phenyl, wherein the group T is the same as describedhereinbefore in (c)(vii); (ii) an unsubstituted, mono-, di-, ortri-substituted aryl group, phenyl or naphthyl; (iii) 9-julolidinyl orthe unsubstituted, mono- or di-substituted heteroaromatic group chosenfrom pyridyl furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl,benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl,carbazoyl, benzopyridyl, indolinyl or fluorenyl, each of said aryl andheteroaromatic substituents in (hh)(ii) and (iii) being independentlychosen from hydroxy, —C(O)U, wherein U being hydroxy, C₁–C₆ alkyl,C_(1–C) ₆ alkoxy, phenyl, mono-substituted phenyl, amino, mono(C₁–C₆)alkylamino, di-(C₁–C₆)alkylamino, morpholino, piperidino orpyrrolidyl; aryl, mono(C₁–C₆) alkoxyaryl, di(C₁–C₆)alkoxyaryl,mono(C₁–C₆)alkylaryl, di(C₁–C₆)alkylaryl, chloroaryl, fluoroaryl, C₃–C₇cycloalkylaryl, C₃–C₇ cycloalkyl, C₃–C₇ cycloalkyloxy, C₃–C₇cycloalkyloxy(C₁–C₆)alkyl, C₃–C₇ cycloalkyloxy(C₁–C₆)alkoxy,aryl(C₁–C₆)alkyl, aryl(C₁–C₆)alkoxy, aryloxy, aryloxy(C₁ –C₆)alkyl,aryloxy(C₁–C₆)alkoxy, mono- or di-(C₁–C₆)alkylaryl (C₁–C₆)alkyl, mono-or di-(C₁–C₆)alkoxyaryl(C₁–C₆)alkyl, mono- ordi-(C₁–C₆)alkylaryl(C₁–C₆)alkoxy, mono- or di-(C₁–C₆)alkoxyaryl(C₁–C₆)alkoxy, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino,diarylamino, piperazino, N-(C₁–C₆)alkylpiperazino, N-arylpiperazino,aziridino, indolino, piperidino, morpholino, thiomorpholino,tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, C₁–C₆ alkyl,C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl, C₁–C₆ alkoxy,mono(C₁–C₆)alkoxy(C₁C₄)alkyl, acryloxy, methacryloxy, bromo, chloro orfluoro, said aryl being chosen from phenyl or naphthyl; (iv) anunsubstituted or mono-substituted group chosen from pyrazolyl,imidazolyl, pyrazolinyl, imidazolinyl, pyrrolinyl, phenothiazinyl,phenoxazinyl, phenazinyl or acridinyl, each of said substituents beingindependently chosen from C₁–C₆ alkyl, C₁–C₆ alkoxy, phenyl, fluoro,chloro or bromo; (v) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being —(CH₂)_(r)— or—O—(CH₂)_(r)—, wherein r being chosen from the integer 1, 2, 3, 4, 5 or6, said substituent being connected to an aryl group which is a memberof another photochromic material, and; (vi) a group represented by oneof the following graphic formulae:

 wherein A being independently chosen in each formula from methylene oroxygen and D being independently chosen in each formula from oxygen orsubstituted nitrogen, provided that when D is substituted nitrogen, A ismethylene; said nitrogen substituents being chosen from hydrogen, C₁–C₆alkyl, or C₂–C₆ acyl; each R₂₀ being independently chosen for eachoccurrence in each formula from C₁–C₆ alkyl, C₁–C₆ alkoxy, hydroxy,chloro or fluoro; R₁₈ and R₁₉ each being independently chosen in eachformula from hydrogen or C₁–C₆ alkyl; and q being chosen from theinteger 0, 1 or 2; (vii) C₁–C₆ alkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, C₁–C₆ alkoxy(C₁–C₄)alkyl, C₃–C₆ cycloalkyl,mono(C₁–C₆)alkoxy(C₃–C₆)cycloalkyl, mono(C₁–C₆)alkyl(C₃–C₆)-cycloalkyl,chloro(C₃–C₆)cycloalkyl, fluoro(C₃–C₆)cyclo-alkyl or C₄–C₁₂bicycloalkyl; (viii) a group represented by the following graphicformula:

 wherein L being chosen from hydrogen or C₁–C₄ alkyl and M being chosenfrom an unsubstituted, mono-, or di-substituted group chosen fromnaphthyl, phenyl, furanyl, or thienyl; each of said group substituentsbeing independently chosen from C₁–C₄ alkyl, C₁–C₄ alkoxy, fluoro, orchloro; or (ix) B and B′ taken together form fluoren-9-ylidene, mono-,or di-substituted fluoren-9-ylidene or a group being independentlychosen from saturated C₃–C₁₂ spiro-monocyclic hydrocarbon rings,saturated C₇–C₁₂ spiro-bicyclic hydrocarbon rings or saturatedC₇–C₁₂spiro-tricyclic hydrocarbon rings; each of said fluoren-9-ylidenesubstituents being independently chosen from C₁–C₄ alkyl, C₁–C₄ alkoxy,fluoro or chloro.
 39. The photochromic article of claim 38 wherein thephotochromic article is adapted to exhibit an unactivated state luminoustransmittance of greater than 80 percent at 23° C., an activated stateluminous transmittance at saturation less than 30 percent when activatedat 23° C. by simulated sunlight from a xenon arc lamp set at 6.7Watts/meter² UVA and 50,000 lumens/meter², and an activated stateluminous transmittance at saturation less than 40 percent when activatedat 28° C. by simulated sunlight from a xenon arc lamp through an UVblocking transparency rendering an irradiance integrated between 380 and420 nanometers of 0.75 Watts/meter² and 1,700 lumens/meter².
 40. Thephotochromic article of claim 38 wherein the UV blocking transparency isa vehicular windshield.
 41. The photochromic article of claim 38 furthercomprising at least one fixed tint dye.
 42. The photochromic article ofclaim 38 wherein said photochromic article is adapted to exhibit aneutral activated color.
 43. The photochromic article of claim 38wherein photochromic material (b) is chosen from: (a) a singlephotochromic compound; (b) a mixture of photochromic compounds; (c) amaterial comprising at least one photochromic compound; (d) a materialto which at least one photochromic compound is chemically bonded; (e)material (c) or (d) further comprising a coating to substantiallyprevent contact of the at least one photochromic compound with externalmaterials; (f) a photochromic polymer; or (g) mixtures thereof.
 44. Thephotochromic article of claim 38 further comprising at least one otherphotochromic material (c) that is different from photochromic material(b).
 45. The photochromic article of claim 44 wherein photochromicmaterial (c) is chosen from: (a) a single photochromic compound; (b) amixture of photochromic compounds; (c) a material comprising at leastone photochromic compound; (d) a material to which at least onephotochromic compound is chemically bonded; (e) material (c) or (d)further comprising a coating to substantially prevent contact of the atleast one photochromic compound with external materials; (f) aphotochromic polymer; or (g) mixtures thereof.
 46. The photochromicarticle of claim 38 further comprising an at least partial coating of anat least partially abrasion resistant coating.
 47. The photochromicarticle of claim 46 further comprising an at least partial coating of anat least partially antireflective coating.
 48. The photochromic articleof claim 38 wherein the substrate comprises at least one photochromicmaterial (b).
 49. The photochromic article of claim 48 wherein thesubstrate further comprises at least one photochromic material (c) thatis different from photochromic material (b).
 50. The photochromicarticle of claim 38 further comprising an at least partial coating of anat least partially cured polymeric coating applied to at least onesurface of the substrate.
 51. The photochromic article of claim 50wherein the at least partially cured polymeric coating comprisesphotochromic material (b).
 52. The photochromic article of claim 51wherein the at least partially cured polymeric coating further comprisesat least one other photochromic material (c) that is different fromphotochromic material (b).
 53. The photochromic article of claim 50wherein the at least partially cured polymeric coating is a polymericcoating of thermoplastic or thermosetting materials.
 54. Thephotochromic article of claim 53 wherein the at least partially curedpolymeric coating is a polymeric coating of thermosetting materialschosen from polyurethanes, aminoplast resins, poly(meth)acrylates,polyanhydrides, polyacrylamides, epoxy resins or polysilanes.
 55. Thephotochromic article of claim 50 further comprising an at least partialcoating of primer interposed between the at least partially curedpolymeric coating and the substrate.
 56. The photochromic article ofclaim 55 further comprising an at least partial coating of an at leastpartially abrasion resistant coating applied to the surface of the atleast partially cured polymeric coating.
 57. The photochromic article ofclaim 56 further comprising an at least partial coating of an at leastpartially antireflective coating.
 58. The photochromic article of claim38 wherein the substrate is chosen from paper, glass, ceramic, wood,masonry, textile, metal or organic polymeric material.
 59. Thephotochromic article of claim 58 wherein the substrate is organicpolymeric material and said organic polymeric material is chosen frompoly(C₁–C₁₂ alkyl methacrylates), poly(oxyalkylene dimethacrylates),poly(alkoxylated phenol methacrylates), cellulose acetate, cellulosetriacetate, cellulose acetate propionate, cellulose acetate butyrate,poly(vinyl acetate), poly(vinyl alcohol), poly(vinyl chloride),poly(vinylidene chloride), thermoplastic polycarbonates, polyesters,polyurethanes, poly(ethylene terephthalate), polystyrene, poly(alphamethylstyrene), copoly(styrene-methylmethacrylate),copoly(styrene-acrylonitrile), polyvinylbutyral or is polymerized frommonomers chosen from bis(allyl carbonate) monomers, polyfunctionalacrylate monomers, polyfunctional methacrylate monomers, diethyleneglycol dimethacrylate monomers, diisopropenyl benzene monomers,ethoxylated bisphenol A dimethacrylate monomers, ethylene glycolbismethacrylate monomers, poly(ethylene glycol) bismethacrylatemonomers, ethoxylated phenol bis methacrylate monomers, alkoxylatedpolyhydric alcohol polyacrylate monomers, styrene monomers, urethaneacrylate monomers, glycidyl acrylate monomers, glycidyl methacrylatemonomers, diallylidene pentaerythritol monomers or mixtures thereof. 60.The photochromic article of claim 59 wherein the substrate is an organicpolymeric material and said organic polymeric material is an opticalelement.
 61. The photochromic article of claim 60 wherein the substrateis an optical element and said optical element is an ophthalmic lens.62. The photochromic article of claim 38 further comprising asuperstrate connected to at least a portion of the substrate, saidsuperstrate comprising at least one organic polymeric material.
 63. Thephotochromic article of claim 62 wherein the superstrate comprisesphotochromic material (b).
 64. The photochromic article of claim 63wherein the superstrate further comprises at least one otherphotochromic material (c) that is different from photochromic material(b).
 65. The photochromic article of claim 62 wherein the superstrate isadheringly bonded to at least a portion of the substrate.
 66. Thephotochromic article of claim 62 wherein the superstrate is an organicpolymeric material chosen from thermosetting or thermoplastic materials.67. The photochromic article of claim 66 wherein the superstrate is athermoplastic material and is polyurethane.
 68. The photochromic articleof claim 62 further comprising an at least partially abrasion resistantfilm superposed on at least a portion of the superstrate.
 69. Thephotochromic article of claim 68 wherein the at least partially abrasionresistant film is an organic polymeric material chosen fromthermoplastic and thermosetting materials.
 70. The photochromic articleof claim 69 wherein the at least partially abrasion resistant film is athermoplastic material and is polycarbonate.
 71. The photochromicarticle of claim 70 further comprising an at least partial coating of anat least partially antireflective coating.
 72. A method for producing aphotochromic article adapted to retain at least 12 percent of the deltaOD measured in the Outdoor Test when tested in the Behind the WindshieldTest comprising: a) obtaining a substrate; b) obtaining an organicphotochromic material (b) adapted to change from an unactivated form toan activated form by exposure to radiation substantially in thewavelength range from 380 to 410 nanometers when measured over a rangeof from 380 to 700 nanometers; c) introducing a photochromic amount ofsaid photochromic material (b) together with said substrate by a methodchosen from: i) introducing photochromic material (b) with the startingmaterials used to form said substrate; ii) at least partially imbibingphotochromic material (b) into at least one surface of said substrate;iii) applying at least a partial coating of a polymeric coatingcomposition comprising photochromic material (b) to at least one surfaceof said substrate; iv) at least partially connecting a superstratecomprising photochromic material (b) to at least one surface of saidsubstrate; or v) combinations of i), ii), ii) or iv), said photochromicmaterial (b) is represented by the following graphic formula XIIIwherein:

 wherein, (aa) R₆₁ is represented by: (i) —SR₆₇, R₆₇ being chosen fromC₁–C₆ alkyl, aryl, mono- or di-substituted aryl, said aryl group beingphenyl or naphthyl and each of said aryl substituents being chosenindependently from C₁–C₆ alkyl, C₁–C₆ alkoxy or halogen; or (ii) anamino group chosen from: (1) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each beingindependently chosen from hydrogen, C₁–C₈ alkyl, aryl, furanyl,benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl,benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl,fluorenyl, C₁–C₈ alkylaryl, C₃–C₂₀ cycloalkyl, C₄–C₂₀ bicycloalkyl,C₅–C₂₀ tricycloalkyl or C₁–C₂₀ alkoxyalkyl and said aryl group beingphenyl or naphthyl; (2) a nitrogen containing ring represented by thefollowing graphic formula:

 wherein each Y being independently chosen for each occurrence from—OH₂—, —CH(R₂₆)—, —C(R₂₆)(R₂₆)—, —CH(aryl)-, —C(aryl)₂— or—C(R₂₆)(aryl)-; X being —Y—, —O—, —S—, —S(O)—, —S(O₂)—, —NH—, —N(R₂₆)—or —N(aryl)-; R₂₆ being C₁–C₆ alkyl; said aryl group being phenyl ornaphthyl, m being chosen from the integer 1, 2 or 3 and p being chosenfrom the integer 0, 1, 2 or 3; provided that when p is 0, X is Y; (3) agroup represented by one of the following graphic formulae:

 wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen, C₁–C₅ alkyl, phenyl ornaphthyl; or the groups R₂₈ and R₂₉ together form a ring of 5 to 8carbon atoms; R₂₇ being chosen independently for each occurrence fromC₁–C₆ alkyl, C₁–C₆ alkoxy, fluoro or chloro and q being chosen from theinteger 0, 1 or 2; (4) unsubstituted, mono- or di- substituted C₄–C₁₈spirobicyclic amine; and (5) unsubstituted, mono- or di- substitutedC₄–C₁₈ spirotricyclic amine; said substituents for (4) and (5) beingindependently chosen for each occurrence from aryl, C₁–C₆ alkyl, C₁–C₆alkoxy or phenyl(C₁–C₆)alkyl; (bb) R₆₁ ′ is independently chosen foreach occurrence from C₁–C₆ alkyl or C₁–C₆ alkoxy and q being chosen fromthe integer 0, 1 or 2; (cc) R₆₂ and R₆₃ are each independently chosenfrom: (i) hydrogen, hydroxy, amino, mono- or di-substituted amino,C₁–C₁₂ alkyl, C₃–C₁₂ alkylidene, C₂–C₁₂ alkylidyne, vinyl, C₃–C₇cycloalkyl, C₁–C₆ alkoxyalkyl, allyl, benzyl, mono-substituted benzyl,chloro, fluoro or —C(O)W″, wherein W″ being hydroxy, C₁–C₆ alkyl, C₁–C₆alkoxy, phenyl, mono-substituted phenyl, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, morpholino, piperidino or pyrrolidyl; said aminosubstituents in (cc)(i) being C₁–C₆ alkyl, phenyl, benzyl or naphthyl;each of said benzyl substituents being C₁–C₆ alkyl or C₁–C₆ alkoxy; (ii)an unsubstituted, mono- di- or tri-substituted group chosen from phenyl,naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl,thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl orindolyl; each of said group substituents in (cc)(ii) being chosenindependently for each occurrence from chloro, fluoro, C₁–C₆ alkyl orC₁–C₆ alkoxy; (iii) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being —(CH₂)_(r)— or—O—(CH₂)_(r)—, wherein r being chosen from the integer 1, 2, 3, 4, 5 or6, said substituent being connected to an aryl group which is a memberof another photochromic material; (iv) —OR_(67′), R_(67′) being chosenfrom C₁–C₆ alkyl, C₁–C₆ acyl, phenyl(C₁–C₃)alkyl, mono C₁–C₆ alkylsubstituted phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substitutedphenyl(C₁–C₃)alkyl, C_(1 –C) ₆ alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl,mono(C₁–C₄)alkyl substituted C₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, allyl, triarylsilyl, triarysilyloxy, tri(C₁–C₆)alkylsilyl,tri(C₁–C₆)alkylsilyloxy, tri(C₁–C₆)alkoxysilyl,tri(C₁-–C₆)alkoxysilyloxy, di(C₁–C₆)alkyl(C₁–C₆ alkoxy)silyl,di(C₁–C₆)alklyl(C₁–C₆alkoxy)silyloxy, di(C₁–C₆)alkoxy(C_(1 –C) ₆alkyl)silyl, di(C₁–C₆)alkoxy(C₁–C₆alkyl)silyloxy, benzoyl,mono-substituted benzoyl, naphthoyl or mono-substituted naphthoyl; eachof said benzoyl and naphthoyl substituents being independently chosenfrom C₁–C₆ alkyl or C₁–C₆ alkoxy; or R_(67′) being —CH(R₆₈)Q″, whereinR₆₈ being chosen from hydrogen or C₁–C₃ alkyl and Q″ being chosen from—CN, —CF₃, or —COOR₆₈; R_(67′) being —C(O)V″, wherein V″ being chosenfrom hydrogen, C₁–C₆ alkoxy, phenoxy, mono- or di-(C₁–C₆)alkylsubstituted phenoxy, mono- or di-(C₁–C₆)alkoxy substituted phenoxy, anunsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl,amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino, phenylamino, mono- ordi-(C₁–C₆)alkyl substituted phenylamino, or mono- or di-(C₁–C₆)alkoxysubstituted phenylamino; each of said aryl group substituents beingindependently chosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (v) —CH(Q′″)₂,Q′″ being chosen from —CN or —COOR₆₉ and R₆₉ being chosen from hydrogen,C₁–C₆ alkyl, phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkyl substitutedphenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl; each of said aryl group substituents being independentlychosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (vi) —OH(R₇₀)G″, R₇₀ beingchosen from hydrogen, C₁–C₆ alkyl or an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, and G″ being chosen from—COOR₆₉, —COR₇₁ or —CH₂OR₇₂ wherein R₇₁, being chosen from hydrogen,C₁–C₆ alkyl, an unsubstituted, mono- or di-substituted aryl group,phenyl or naphthyl, amino, mono(C₁–C₆)alkylamino, di(C₁–C₆)alkylamino,phenylamino, mono- or di-(C₁–C₆)alkyl substituted phenylamino, mono- ordi-(C₁–C₆)alkoxy substituted phenylamino, diphenylamino, mono- ordi(C₁–C₆)alkyl substituted diphenylamino, mono- or di(C₁–C₆)alkoxysubstituted diphenylamino, morpholino or piperidino; R₇₂ being chosenfrom hydrogen, —C(O)R₆₉, C₁–C₆ alkyl, C₁–C₃ alkoxy(C₁–C₆)alkyl,phenyl(C₁–C₃)alkyl, mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl, each of said aryl group substituents being independentlychosen from C₁–C₆ alkyl or C₁–C₆ alkoxy; (vii) the group T wherein thegroup T is represented by the formula:-G[(OC₂H₄)_(x)(OC₃H6)_(y)(OC₄H₈)_(z)]G′—[(OC₂H₄)_(y)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′ wherein -G being chosen from—C(O)— or —CH₂—, G′ being chosen from C₁–C₃ alkoxy or a polymerizablegroup, x, y and z each being independently chosen from a number between0 and 50, and the sum of x, y and z being between 2 and 50: or (viii)R₆₂ and R₆₃ together form an oxo group or a substituted or unsubstitutedspiro-carbocyclic ring containing 3 to 6 carbon atoms or a substitutedor unsubstituted spiro-heterocyclic group containing 1 or 2 oxygen atomsand 3 to 6 carbon atoms including the spirocarbon atom, saidspiro-carbocyclic ring and spiro-heterocyclic group being annellatedwith 0, 1 or 2 benzene rings, said substituents being hydrogen or C₁–C₆alkyl; (dd) R₆₄ is hydrogen or C₁–C₆ alkyl (ee) R₆₅ is hydrogen or C₁–C₆alkyl; (ff) R₆₆ is chosen from hydrogen, C₁–C₆ alkyl or R_(a), saidR_(a) chosen from: (i) —OR₇₃, R₇₃ being chosen from phenyl(C₁–C₃)alkyl,C₁–C₆ alkyl, mono(C₁–C₆)alkyl substituted phenyl(C₁–C₃)alkyl,mono(C₁–C₆)alkoxy substituted phenyl(C₁–C₃)alkyl,C₁–C₆alkoxy(C₂–C₄)alkyl, C₃–C₇ cycloalkyl, mono(C₁–C₄)alkyl substitutedC₃–C₇ cycloalkyl, C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl, allyl or—CH(R₆₈)Q″ described in (cc)(i);

 and (gg) B and B′ are each independently chosen from (i)mono-T-substituted phenyl, wherein the group T is the same as describedhereinbefore in (cc)(vii); (ii) an unsubstituted, mono-, di-, ortri-substituted aryl group, phenyl or naphthyl; (iii) 9-julolidinyl orthe unsubstituted, mono- or di-substituted heteroaromatic group chosenfrom pyridyl furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl,benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl,carbazoyl, benzopyridyl, indolinyl or fluorenyl, each of said aryl andheteroaromatic substituents in (hh)(ii) and (iii) being independentlychosen from hydroxy, —C(O)U, wherein U being hydroxy, C₁–C₆ alkyl, C₁–C₆alkoxy, phenyl, mono-substituted phenyl, amino, mono (C₁–C₆)alkylamino,di-(C₁–C₆)alkylamino, morpholino, piperidino or pyrrolidyl; aryl,mono(C₁–C₆)alkoxyaryl, di(C₁–C₆)alkoxyaryl, mono(C₁–C₆)alkylaryl,di(C₁–C₆)alkylaryl, chloroaryl, fluoroaryl, C₃–C₇ cycloalkylaryl, C₃–C₇cycloalkyl, C₃–C₇ cycloalkyloxy, C₃–C₇ cycloalkyloxy(C₁–C₆)alkyl, C₃–C₇cycloalkyloxy(C₁–C₆)alkoxy, aryl(C₁–C₆)alkyl, aryl(C₁–C₆)alkoxy,aryloxy, aryloxy(C₁–C₆)alkyl, aryloxy(C₁–C₆)alkoxy, mono- ordi-(C₁–C₆)alkylaryl(C₁–C₆)alkyl, mono- ordi-(C₁–C₆)alkoxyaryl(C₁–C₆)alkyl, mono- ordi-(C₁–C₆)alkylaryl(C₁–C₆)alkoxy, mono- ordi-(C₁–C₆)alkoxyaryl(C₁–C₆)alkoxy, amino, mono(C₁–C₆)alkylamino,di(C₁–C₆)alkylamino, diarylamino, piperazino, N—(C₁–C₆)alkylpiperazino,N-arylpiperazino, aziridino, indolino, piperidino, morpholino,thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl,C₁–C₆ alkyl, C₁–C₆ chloroalkyl, C₁–C₆ fluoroalkyl, C₁–C₆ alkoxy,mono(C₁–C₆)alkoxy(C₁–C₄)alkyl, acryloxy, methacryloxy, bromo, chloro orfluoro, said aryl being chosen from phenyl or naphthyl; (iv) anunsubstituted or mono-substituted group chosen from pyrazolyl,imidazolyl, pyrazolinyl, imidazolinyl, pyrrolinyl, phenothiazinyl,phenoxazinyl, phenazinyl or acridinyl, each of said substituents beingindependently chosen from C₁–C₆ alkyl, C₁–C₆ alkoxy, phenyl, fluoro,chloro or bromo; (v) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being —(CH₂)_(r)— or—O—(CH₂)_(r)—, wherein r being chosen from the integer 1, 2, 3, 4, 5 or6, said substituent being connected to an aryl group which is a memberof another photochromic material, and; (vi) a group represented by oneof the following graphic formulae:

 wherein A being independently chosen in each formula from methylene oroxygen and D being independently chosen in each formula from oxygen orsubstituted nitrogen, provided that when D is substituted nitrogen, A ismethylene; said nitrogen substituents being chosen from hydrogen, C₁–C₆alkyl, or C₂–C₆ acyl; each R₂₀ being independently chosen for eachoccurrence in each formula from C₁–C₆ alkyl, C₁–C₆ alkoxy, hydroxy,chloro or fluoro; R₁₈ and R₁₉ each being independently chosen in eachformula from hydrogen or C₁–C₆ alkyl; and q being chosen from theinteger 0, 1 or 2; (vii) C₁–C₆ alkyl, C₁–C₆ chloroalkyl, C₁–C₆fluoroalkyl, C₁–C₆ alkoxy(C₁–C₄)alkyl, C₃–C₆ cycloalkyl,mono(C₁–C₆)alkoxy(C₃–C₆)cycloalkyl, mono(C₁–C₆)alkyl(C₃–C₆)-cycloalkyl,chloro(C₃–C₆)cycloalkyl, fluoro(C₃–C₆)cyclo-alkyl or C₄–C₁₂bicycloalkyl; (viii) a group represented by the following graphicformula:

 wherein L being chosen from hydrogen or C₁–C₄ alkyl and M being chosenfrom an unsubstituted, mono-, or di-substituted group chosen fromnaphthyl, phenyl, furanyl, or thienyl; each of said group substituentsbeing independently chosen from C₁–C₄ alkyl, C₁–C₄ alkoxy, fluoro, orchloro; or (ix) B and B′ taken together form fluoren-9-ylidene, mono-,or di-substituted fluoren-9-ylidene or a group being independentlychosen from saturated C₃–C₁₂ spiro-monocyclic hydrocarbon rings,saturated C₇–C₁₂ spiro-bicyclic hydrocarbon rings or saturated C₇–C₁₂spiro-tricyclic hydrocarbon rings; each of said fluoren-9-ylidenesubstituents being independently chosen from C₁–C₄ alkyl, C₁–C₄ alkoxy,fluoro or chloro.
 73. The method of claim 72 further comprising adding aphotochromic material (c) that is different from photochromic material(b), in (c) (i), (ii), (iii), (iv) or (v).
 74. The method of claim 72further comprising adding a fixed tint dye in (c) (i), (ii), (iii), (iv)or (v).